52574-08-0

Basic information

• Product Name: S-ACETAMIDOMETHYL-3-MERCAPTOPROPIONIC ACID
• Synonyms: S-ACETAMIDOMETHYL-3-MERCAPTOPROPIONIC ACID;S-ACETAMIDOMETHYL-DEAMINO-CYSTEINE;S-(ACETYL-AMINOMETHYL)-3-MERCAPTOPROPIONIC ACID;MPA(ACM)-OH;(ACM)SCH2CH2COOH;3-(ACETYLAMINOMETHYLSULFANYL)PROPIONIC ACID;3-(ACETAMIDO-METHYLSULFANYL)-PROPIONIC ACID;3-MERCAPTOPROPIONIC ACID(ACM)
• CAS NO: 52574-08-0
• Molecular Formula: C₆H₁₁NO₃S
• Molecular Weight: 177.22
• Product Categories: Other Reagents
• Mol File: 52574-08-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 240C
• Boiling Point: 430.1±30.0 °C(Predicted)
• Appearance: /
• Density: 1.247±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 4.31±0.10(Predicted)
• CAS DataBase Reference: S-ACETAMIDOMETHYL-3-MERCAPTOPROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: S-ACETAMIDOMETHYL-3-MERCAPTOPROPIONIC ACID(52574-08-0)
• EPA Substance Registry System: S-ACETAMIDOMETHYL-3-MERCAPTOPROPIONIC ACID(52574-08-0)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38-36
• Safety Statements: 26-36
• Hazardous Substances Data: 52574-08-0(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Synthetic route

N-(hydroxymethyl)acetamide (625-51-4) + 3-mercaptopropionic acid (107-96-0) → 3-{[(acetylamino)methyl]sulfanyl}-propionic acid (52574-08-0)

Conditions	Yield
In trifluoroacetic acid for 0.5h; Ambient temperature;	62%

3-(tritylthio) propanoic acid (27144-18-9) + N-(hydroxymethyl)acetamide (625-51-4) → 3-{[(acetylamino)methyl]sulfanyl}-propionic acid (52574-08-0)

Conditions	Yield
With trifluoroacetic acid for 2.5h;	17.1%

3-{[(acetylamino)methyl]sulfanyl}-propionic acid (52574-08-0) + methyl (S)-7-amino-3{[(tert-butoxy)carbonyl]amino}heptanoate → methyl (S)-7-({3-[(acetylamino)methylsulfanyl]propionyl}amino)-3-{[(tert-butoxy)carbonyl]amino}haptanoate (329348-46-1)

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In chloroform at 0 - 20℃; for 23h;	92%

3-{[(acetylamino)methyl]sulfanyl}-propionic acid (52574-08-0) + Z-Gly-Glu(O-But)-Arg(Adoc)2-OH (86095-68-3) → Acm-SCH2.CH2CO.Gly.Glu.(OBut).Arg(Adoc)2OH (86095-70-7)

Conditions	Yield
With 4-methyl-morpholine; pivaloyl chloride In N,N-dimethyl-formamide for 2h;	59%

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + 3-{[(acetylamino)methyl]sulfanyl}-propionic acid (52574-08-0) + (R)-2-(tert-butoxycarbonyl(methyl)amino)-3-methylbutanoic acid (13850-91-4, 45170-31-8, 89536-85-6) → (S)-2-((R)-2-{[3-(Acetylamino-methylsulfanyl)-propionyl]-methyl-amino}-3-methyl-butyrylamino)-3-phenyl-propionic acid

Conditions	Yield
Multistep reaction;

(3S)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinole-3-carboxylic acid (115962-35-1, 144069-68-1, 78879-20-6) + 3-{[(acetylamino)methyl]sulfanyl}-propionic acid (52574-08-0) + (R)-2-(tert-butoxycarbonyl(methyl)amino)-3-methylbutanoic acid (13850-91-4, 45170-31-8, 89536-85-6) → (S)-2-((R)-2-{[3-(Acetylamino-methylsulfanyl)-propionyl]-methyl-amino}-3-methyl-butyryl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid

Conditions	Yield
Multistep reaction;

3-{[(acetylamino)methyl]sulfanyl}-propionic acid (52574-08-0) + chloro(chlorosulfanyl)methanone (2757-23-5) + N-methylaniline (100-61-8) → S-[(N-methyl-N-phenylcarbamoyl)sulfenyl]-β-thiopropionic acid

Conditions	Yield
1.) CHCl3, 10 min, 2.) CHCl3, 20 min; Yield given. Multistep reaction;

(chlorocarbonyl)disulfanyl chloride (79341-73-4) + 3-{[(acetylamino)methyl]sulfanyl}-propionic acid (52574-08-0) + N-methylaniline (100-61-8) → S-[(N-methyl-N-phenylcarbamoyl)disulfanyl]-β-thiopropionic acid

Conditions	Yield
1.) CHCl3, 10 min, 2.) CHCl3, 20 min; Yield given. Multistep reaction;

3-{[(acetylamino)methyl]sulfanyl}-propionic acid (52574-08-0) + Arg-Val-Tyr-Val-His-Pro-Phe-OH-resin → [Mpr(S-Acm)(1)Val(5)]angiotensin II (184353-68-2)

Conditions	Yield
With hydrogen fluoride; benzotriazol-1-ol; dicyclohexyl-carbodiimide 1.) DMF/CH2Cl2; Multistep reaction;

N-Fmoc L-Phe (35661-40-6) + Fmoc-Trp-OH (35737-15-6) + 3-{[(acetylamino)methyl]sulfanyl}-propionic acid (52574-08-0) + N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-(2-((acetamidomethyl)thio)ethyl)glycine (425428-82-6) + Fmoc-D-Trp-OH + Fmoc-Lys-OH Fmoc-Thr(t-Bu)-OH → 2-[(7S,10S,13S,16R,19S,22S)-13-(4-Amino-butyl)-7,22-dibenzyl-10-((R)-1-hydroxy-ethyl)-16,19-bis-(1H-indol-3-ylmethyl)-6,9,12,15,18,21,24-heptaoxo-1,2-dithia-5,8,11,14,17,20,23-heptaaza-cyclohexacos-5-yl]-acetamide

Conditions	Yield
Multistep reaction.;

N-Fmoc L-Phe (35661-40-6) + Fmoc-Trp-OH (35737-15-6) + 3-{[(acetylamino)methyl]sulfanyl}-propionic acid (52574-08-0) + N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-(2-((acetamidomethyl)thio)ethyl)glycine (425428-82-6) + Fmoc-D-Trp-OH + Fmoc-Lys-OH Fmoc-Thr(t-Bu)-OH → 2-[(7S,10S,13S,16R,19S,22S,25R)-25-Amino-13-(4-amino-butyl)-7,22-dibenzyl-10-((R)-1-hydroxy-ethyl)-16,19-bis-(1H-indol-3-ylmethyl)-6,9,12,15,18,21,24-heptaoxo-1,2-dithia-5,8,11,14,17,20,23-heptaaza-cyclohexacos-5-yl]-acetamide

Conditions	Yield
Multistep reaction.;

3-{[(acetylamino)methyl]sulfanyl}-propionic acid (52574-08-0) → (S)-7-({3-[(acetylamino)methylsulfanyl]propionyl}amino)-3-{[(tert-butoxy)carbonyl]amino}haptanoic acid

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / Et3N; EDC; HOBt / CHCl3 / 23 h / 0 - 20 °C 2: 74 percent / aq. NaOH / methanol / 21.5 h View Scheme

Upstream product

• 27144-18-9 3-(tritylthio) propanoic acid 
• 625-51-4 N-(hydroxymethyl)acetamide 
• 107-96-0 3-mercaptopropionic acid 

Downstream Products

• 184353-68-2 [Mpr(S-Acm)⁽¹⁾Val⁽⁵⁾]angiotensin II 

Relevant articles and documents

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