2544-31-2

Basic information

• Product Name: 2-Amino-3-[(4-methoxybenzyl)thio]propanoic acid
• Synonyms: H-CYS(PMEOBZL)-OH;H-CYS(MEOBZL)-OH;H-CYS(MOB)-OH;H-CYS(4-MEOBZL)-OH;H-CYS(4-MOB)-OH;CYSTEINE(MOB)-OH;S-4-METHOXYBENZYL-L-CYSTEINE;S-P-METHOXYBENZYL-L-CYSTEINE
• CAS NO: 2544-31-2
• Molecular Formula: C₁₁H₁₅NO₃S
• Molecular Weight: 241.31
• Product Categories: Pharmaceutical Intermediates;Amino Acids Derivatives;Amino Acids;Cysteine [Cys, C];Amino Acids and Derivatives
• Mol File: 2544-31-2.mol
• Article Data: 9

Chemical Properties

• Melting Point: 198-199 °C(Solv: water (7732-18-5))
• Boiling Point: 417.6 °C at 760 mmHg
• Flash Point: 206.4 °C
• Appearance: /Solid
• Density: 1.257 g/cm³
• Vapor Pressure: 1.01E-07mmHg at 25°C
• Refractive Index: 1.59
• Storage Temp.: Store at RT.
• PKA: 2.08±0.10(Predicted)
• CAS DataBase Reference: 2-Amino-3-[(4-methoxybenzyl)thio]propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-3-[(4-methoxybenzyl)thio]propanoic acid(2544-31-2)
• EPA Substance Registry System: 2-Amino-3-[(4-methoxybenzyl)thio]propanoic acid(2544-31-2)

Safety Data

• Hazardous Substances Data: 2544-31-2(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder

InChI:InChI=1/C11H15NO3S/c1-15-9-4-2-8(3-5-9)6-16-7-10(12)11(13)14/h2-5,10H,6-7,12H2,1H3,(H,13,14)/t10-/m0/s1

Synthetic route

Z(OMe)-Cys(MBzl)-OH (23619-36-5) → S-(4-methoxybenzyl)-L-cysteine (2544-31-2)

Conditions	Yield
With methanesulfonic acid; 3-methyl-phenol In dichloromethane at 25℃; for 0.5h;	100%
Multi-step reaction with 3 steps 1: aq. sodium perborate / ethyl acetate 2: CF3CO2H / diethyl ether 3: HF View Scheme

L-Cysteine (52-90-4) + p-methoxybenzyl chloride (824-94-2) → S-(4-methoxybenzyl)-L-cysteine (2544-31-2)

Conditions	Yield
With trifluoroacetic acid In dichloromethane 1.) 0 deg C, 1 h; 2.) RT, 30 min;	81%
Stage #1: p-methoxybenzyl chloride With hydrogenchloride In diethyl ether; water for 3h; Stage #2: L-Cysteine With sodium hydroxide In diethyl ether; water at 20℃; for 2h;	64%
With ammonia

L-Cysteine (52-90-4) + 4-Methoxybenzyl alcohol (105-13-5) → S-(4-methoxybenzyl)-L-cysteine (2544-31-2)

Conditions	Yield
Stage #1: 4-Methoxybenzyl alcohol With hydrogenchloride In diethyl ether; water for 3h; Stage #2: L-Cysteine With sodium hydroxide In diethyl ether; ethanol; water at 20℃; for 2h; Stage #3: With hydrogenchloride In diethyl ether; ethanol; water at 0℃; pH=7;	64%
Stage #1: 4-Methoxybenzyl alcohol With hydrogenchloride In diethyl ether Stage #2: L-Cysteine With sodium hydroxide In diethyl ether; ethanol; water at 20℃; for 2h; Stage #3: With hydrogenchloride In diethyl ether; ethanol; water at 0℃; pH=7;	64%
Stage #1: 4-Methoxybenzyl alcohol With hydrogenchloride In diethyl ether; water for 3h; Stage #2: L-Cysteine With sodium hydroxide In diethyl ether; ethanol; water at 20℃; for 2h; Stage #3: With hydrogenchloride In diethyl ether; ethanol; water pH=7;	64%
With trifluoroacetic acid In dichloromethane

L-Cysteine (52-90-4) + 4-methoxybenzyl hydrazinecarboxylate (18912-37-3) → S-(4-methoxybenzyl)-L-cysteine (2544-31-2)

Conditions	Yield
With trifluoroacetic acid

(R)-2-(4-Methoxy-phenyl)-thiazolidine-4-carboxylic acid (222404-25-3) → S-(4-methoxybenzyl)-L-cysteine (2544-31-2)

Conditions	Yield
With triethylsilane; trifluoroacetic acid In dichloromethane Ambient temperature;

(R)-2-Amino-3-(4-methoxy-phenylmethanesulfinyl)-propionic acid (73243-09-1) → S-(4-methoxybenzyl)-L-cysteine (2544-31-2)

Conditions	Yield
With hydrogen fluoride

Z(OMe)-Cys(MBzl)(O)-OH (73285-37-7) → S-(4-methoxybenzyl)-L-cysteine (2544-31-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: CF3CO2H / diethyl ether 2: HF View Scheme

l-cysteine hydrochloride (52-89-1) + p-OCH3-C6H4-CH2-X, X=Cl or Br → S-(4-methoxybenzyl)-L-cysteine (2544-31-2)

Conditions	Yield
With sodium hydroxide In ethanol; chloroform; water at 20℃;

S-(4-methoxybenzyl)-L-cysteine (2544-31-2) → L-Cysteine (52-90-4)

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate; methyl-phenyl-thioether In trifluoroacetic acid at 0℃; for 0.5h; Product distribution; New peptide deprotection procedure: hard-soft acid-base concept; the role of soft bases (thioanisole, dimethylsulfide, diphenylsulfide) employed.;	100%
With trifluoroacetic acid In dichloromethane at 20℃; Rate constant;

di-tert-butyl dicarbonate (24424-99-5) + S-(4-methoxybenzyl)-L-cysteine (2544-31-2) → N-(tert-butyloxycarbonyl)-S-(4-methoxybenzyl)cysteine (18942-46-6)

Conditions	Yield
Stage #1: di-tert-butyl dicarbonate; S-(4-methoxybenzyl)-L-cysteine With potassium carbonate In tetrahydrofuran; water at 20℃; for 2h; Stage #2: With hydrogenchloride In water at 0℃; pH=3;	99%
Stage #1: di-tert-butyl dicarbonate; S-(4-methoxybenzyl)-L-cysteine With potassium carbonate In tetrahydrofuran; water at 20℃; for 2h; Stage #2: With hydrogenchloride In water at 0℃; pH=3;	99%
With potassium carbonate In tetrahydrofuran; water at 20℃; for 2h;	99%
With potassium carbonate In tetrahydrofuran; water at 20℃; for 2h;	99%
In tetrahydrofuran; water Ambient temperature; pH=8; Yield given;

S-(4-methoxybenzyl)-L-cysteine (2544-31-2) → L-cystine (56-89-3)

Conditions	Yield
With Methyltrichlorosilane; 1,1'-sulfinylbisbenzene at 4℃; for 0.166667h;	95%
With methoxybenzene; thallium(III) trifluoroacetate In trifluoroacetic acid at 0℃; for 1h;	86.7%
With methoxybenzene; thallium(III) trifluoroacetate In trifluoroacetic acid at 0℃; for 1h; Product distribution; cleavage various S-protecting groups of cystein;	86.7%

S-(4-methoxybenzyl)-L-cysteine (2544-31-2) + (R)-2-Amino-3-(4-methoxy-phenylmethanesulfinyl)-propionic acid (73243-09-1) → L-cystine (56-89-3)

Conditions	Yield
With dimethylsulfide; trifluorormethanesulfonic acid In trifluoroacetic acid at 0℃; for 1h;	92.2%

S-(4-methoxybenzyl)-L-cysteine (2544-31-2) + trichloromethyl chloroformate (503-38-8) → 4-methoxybenzylcysteine N-carboxy anhydride

Conditions	Yield
In tetrahydrofuran at 55℃; for 0.5h; Temperature;	87%

S-(4-methoxybenzyl)-L-cysteine (2544-31-2) + H-Cys(Acm)(O)-OH (75893-05-9) → L-cystine (56-89-3)

Conditions	Yield
With dimethylsulfide In trifluoroacetic acid at 25℃; for 1h;	85.3%

S-(4-methoxybenzyl)-L-cysteine (2544-31-2) + 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile (58632-95-4) → N-(tert-butyloxycarbonyl)-S-(4-methoxybenzyl)cysteine (18942-46-6)

Conditions	Yield
With triethylamine In 1,4-dioxane; water for 3h;	83%

S-(4-methoxybenzyl)-L-cysteine (2544-31-2) + N-tert-butyloxycarbonyl-L-α-aminoadipic acid α-p-methoxybenzyl ester (790244-47-2) → N-tert-butyloxycarbonyl-α-p-methoxybenzyl-δ-(L-α-aminoadipoyl)-S-p-methoxybenzyl-L-cysteine (1041170-88-0)

Conditions	Yield
Stage #1: N-tert-butyloxycarbonyl-L-α-aminoadipic acid α-p-methoxybenzyl ester With triethylamine; isobutyl chloroformate In tetrahydrofuran at -12℃; for 0.5h; Stage #2: S-(4-methoxybenzyl)-L-cysteine With triethylamine In tetrahydrofuran; water at 0 - 20℃; for 1.83333h;	82%

S-(4-methoxybenzyl)-L-cysteine (2544-31-2) + 2,2-dimethoxy-propane (77-76-9) → S-<(4-methoxyphenyl)methyl>-L-cysteine methyl ester hydrochloride (71449-22-4)

Conditions	Yield
With hydrogenchloride	79%

ethanol (64-17-5) + S-(4-methoxybenzyl)-L-cysteine (2544-31-2) → (R)-2-amino-3-(4-methoxy-benzylsulfanyl)propionic acid ethyl ester hydrochloride (156757-43-6)

Conditions	Yield
With acetyl chloride at 50℃; for 12h;	69%

S-(4-methoxybenzyl)-L-cysteine (2544-31-2) + (S)-2-(4-Methoxy-benzyloxycarbonylamino)-succinamic acid 4-nitro-phenyl ester (23931-69-3) → Z(OMe)-Asn-Cys(MBzl)-OH (96105-49-6)

Conditions	Yield
With triethylamine In water; N,N-dimethyl-formamide for 24h; Ambient temperature;	57%

S-(4-methoxybenzyl)-L-cysteine (2544-31-2) → azido-Cys(4-MeO-Bzl)

Conditions	Yield
With triflic azide; potassium carbonate; copper(II) sulfate In methanol; dichloromethane; water at 20℃;	41%

S-(4-methoxybenzyl)-L-cysteine (2544-31-2) + (R)-3-(Adamantane-1-sulfinyl)-2-amino-propionic acid → L-cystine (56-89-3)

Conditions	Yield
With dimethylsulfide; trifluorormethanesulfonic acid In trifluoroacetic acid at 0℃; for 1h;	15.5%

N-(tert-butyloxycarbonyl) azide (1070-19-5) + S-(4-methoxybenzyl)-L-cysteine (2544-31-2) → N-(tert-butyloxycarbonyl)-S-(4-methoxybenzyl)cysteine (18942-46-6)

S-(4-methoxybenzyl)-L-cysteine (2544-31-2) + benzyl chloroformate (501-53-1) → Z-Cys(BzlOMe)-OH (3081-32-1)

S-(4-methoxybenzyl)-L-cysteine (2544-31-2) + N-(4-methoxybenzyloxycarbonyl)-α-(4-methoxybenzylester)-δ-L-α-aminoadipic acid (58635-29-3) → <(N-4-methoxybenzyloxycarbonyl)-(α-4-methoxybenzyl)-δ-(L-α-aminoadipoyl)>-S-(4-methoxybenzyl)-L-cysteine (111360-78-2, 131478-88-1)

Conditions	Yield
With triethylamine; isobutyl chloroformate 1) THF, -15 deg C, 30 min, 2) H2O, RT, 50 min; Yield given. Multistep reaction;
With triethylamine; isobutyl chloroformate 1) THF; Multistep reaction;

S-(4-methoxybenzyl)-L-cysteine (2544-31-2) + Boc-Lys(Z)-Thr-Phe-Thr-Ser-NHNH2 (58290-08-7) → Boc-Lys(Z)-Thr-Phe-Thr-Ser-Cys(MBzl)-OH (85641-07-2)

Conditions	Yield
With hydrogenchloride; tert.-butylnitrite; triethylamine 1) THF, DMF, 15 min, -15 deg C 2) THF, DMF, 0 deg C, 24 h, room temp.,48 h; Yield given. Multistep reaction;

S-(4-methoxybenzyl)-L-cysteine (2544-31-2) + 2,2-dimethoxy-propane (77-76-9) → S-p-methoxybenzyl-L-cysteine methyl ester (61314-87-2)

Conditions	Yield
With hydrogenchloride; sodium carbonate Multistep reaction;

S-(4-methoxybenzyl)-L-cysteine (2544-31-2) + Z(OMe)-Ser-NHNH2 (3481-31-0) → Z(OMe)-Ser-Cys(CH2PhOMe)-OH (56936-26-6)

Conditions	Yield
(i) isopentyl nitrite, HCl, (ii) /BRN= 2055074/, aq. Et3N; Multistep reaction;

S-(4-methoxybenzyl)-L-cysteine (2544-31-2) + 2-nitrobenzenesulfenyl chloride (7669-54-7) → (R)-3-(4-Methoxy-benzylsulfanyl)-2-(2-nitro-phenylsulfanylamino)-propionic acid

Conditions	Yield
With sodium hydroxide In 1,4-dioxane

S-(4-methoxybenzyl)-L-cysteine (2544-31-2) → H-Asn-Cys(MBzl)-OH (96105-50-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 57 percent / Et3N / dimethylformamide; H2O / 24 h / Ambient temperature 2: TFA-anisole View Scheme

S-(4-methoxybenzyl)-L-cysteine (2544-31-2) → H-Cys(MBzl)-Asn-Cys(MBzl)-OMe (96105-54-3)

Conditions	Yield
Multi-step reaction with 5 steps 1: 57 percent / Et3N / dimethylformamide; H2O / 24 h / Ambient temperature 2: TFA-anisole 3: 82 percent / Et3N / dimethylformamide / 12 h / Ambient temperature 4: 88 percent / dimethylformamide; diethyl ether 5: TFA-anisole View Scheme

Upstream product

• 52-90-4 L-Cysteine 
• 18912-37-3 4-methoxybenzyl hydrazinecarboxylate 
• 52-89-1 l-cysteine hydrochloride 
• 73285-37-7 Z(OMe)-Cys(MBzl)(O)-OH 
• 73243-09-1 (R)-2-Amino-3-(4-methoxy-phenylmethanesulfinyl)-propionic acid 
• 105-13-5 4-Methoxybenzyl alcohol 
• 23619-36-5 Z(OMe)-Cys(MBzl)-OH 
• 222404-25-3 (R)-2-(4-Methoxy-phenyl)-thiazolidine-4-carboxylic acid 
• 824-94-2 p-methoxybenzyl chloride 

Downstream Products

• 3081-32-1 Z-Cys(BzlOMe)-OH 
• 18942-46-6 N-(tert-butyloxycarbonyl)-S-(4-methoxybenzyl)cysteine 
• 56-89-3 L-cystine 
• 96105-49-6 Z(OMe)-Asn-Cys(MBzl)-OH 
• 111360-78-2 <(N-4-methoxybenzyloxycarbonyl)-(α-4-methoxybenzyl)-δ-(L-α-aminoadipoyl)>-S-(4-methoxybenzyl)-L-cysteine 
• 85641-07-2 Boc-Lys(Z)-Thr-Phe-Thr-Ser-Cys(MBzl)-OH 
• 52-90-4 L-Cysteine 
• 156757-43-6 (R)-2-amino-3-(4-methoxy-benzylsulfanyl)propionic acid ethyl ester hydrochloride 
• 71449-22-4 S-<(4-methoxyphenyl)methyl>-L-cysteine methyl ester hydrochloride 
• 1041170-88-0 N-tert-butyloxycarbonyl-α-p-methoxybenzyl-δ-(L-α-aminoadipoyl)-S-p-methoxybenzyl-L-cysteine 
• 101035-11-4 N-Carbobenzoxy-S-(4-methoxy-benzyl)-L-cysteinyl-glycin-ethylester 
• 100232-14-2 N-Carbobenzoxy-S-(4-methoxy-benzyl)-L-cysteinyl-glycin 
• 92034-35-0 S-(4-Methoxy-benzyl)-L-cysteinyl-glycin 
• 3081-33-2 N-Benzyloxycarbonyl-S-(4-methoxy-benzyl)-L-cystein-(4-nitro-phenylester) 

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