3-Amino-4-[(1-benzyl-2-methoxy-2-oxoethyl)amino]-4-oxobutanoic acid

Base Information

• Chemical Name: 3-Amino-4-[(1-benzyl-2-methoxy-2-oxoethyl)amino]-4-oxobutanoic acid
• CAS No.: 25548-16-7
• Molecular Formula: C14H18 N2 O5
• Molecular Weight: 294.307
• Hs Code.: 2924293000
• DSSTox Substance ID: DTXSID90274359,DTXSID80860285
• ChEMBL ID: CHEMBL312245
• Mol file: 25548-16-7.mol

Synonyms:25548-16-7;3-Amino-4-[(1-benzyl-2-methoxy-2-oxoethyl)amino]-4-oxobutanoic acid;Phenylalanine,a-aspartyl-, 2-methyl ester;methyl alpha-aspartylphenylalaninate;3-amino-4-[(1-methoxy-1-oxo-3-phenylpropan-2-yl)amino]-4-oxobutanoic acid;L-Phenylalanine, L-.alpha.-aspartyl-, 2-methyl ester;3-Amino-4-((1-methoxy-1-oxo-3-phenylpropan-2-yl)amino)-4-oxobutanoic acid;SMR001550628;L-Aspartame;MFCD00002724;NCGC00095160-01;N-(L-a-Aspartyl)-L-phenylalanine methyl ester;SCHEMBL3637;MLS003883739;MLS006011904;CERAPP_20629;CHEMBL312245;DTXSID80860285;DTXSID90274359;CHEBI:177838;IAOZJIPTCAWIRG-UHFFFAOYSA-N;HMS3370L06;HMS3655P11;APM;Canderel;L-alpha-aspartyl-L-phenylalanine-methylester;(S)-3-Amino-4-(((S)-1-methoxy-1-oxo-3-phenylpropan-2-yl)amino)-4-oxobutanoic acid;BCP31846;BBL009963;CCG-49864;MFCD00176858;STK801364;AKOS005613003;NCGC00095160-02;Phenylalanine,a-aspartyl-,2-methyl ester;AS-12189;SY012642;AM20060824;CS-0450210;FT-0614963;FT-0627714;L-Phenylalanine,l-a-aspartyl-,2-methyl ester;L-.alpha.-Aspartyl-L-phenylalanine methyl ester;L001103;N-L-.alpha.-Aspartyl-L-phenylalanine methyl ester;SR-01000639290;SR-01000639290-1;SR-01000639290-2;3-Amino-N-(.alpha.-methoxycarbonylphenethyl) succinamic acid;3-Amino-N-(.alpha.-carboxyphenethyl)succinamic acid N-methyl ester;3-amino-4-(1-methoxy-1-oxo-3-phenylpropan-2-ylamino)-4-oxobutanoic acid;3-Amino-4-[(1-benzyl-2-methoxy-2-oxoethyl)amino]-4-oxobutanoic acid #;SC-1886;SC1886;SC 1886;Nutrasweet;Asp-Phe methyl ester;Asp-phe-ome;Succinamic acid, 3-amino-N-(.alpha.-carboxyphenethyl)-, N-methyl ester, stereoisomer

Chemical Property of 3-Amino-4-[(1-benzyl-2-methoxy-2-oxoethyl)amino]-4-oxobutanoic acid

Chemical Property:

• Melting Point: 248oC
• Boiling Point: 535.8±50.0 °C(Predicted)
• PKA: 3.71±0.10(Predicted)
• PSA: 118.72000
• Density: 1.280±0.06 g/cm3(Predicted)
• LogP: 0.78010
• XLogP3: -2.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 294.12157168
• Heavy Atom Count: 21
• Complexity: 380

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:Irritating to eyes, respiratory system and skin.
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S37/39:Wear suitable g

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(CC1=CC=CC=C1)NC(=O)C(CC(=O)O)N

Technology Process of 3-Amino-4-[(1-benzyl-2-methoxy-2-oxoethyl)amino]-4-oxobutanoic acid

There total 2 articles about 3-Amino-4-[(1-benzyl-2-methoxy-2-oxoethyl)amino]-4-oxobutanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride (7524-50-7) + L-aspartic acid N-thiocarboxyanhydride (77217-04-0,82522-65-4) → L-Asp-L-Phe-OMe (22839-47-0,7421-84-3) + aspartame (25548-16-7,7421-84-3)

Guidance literature:

With hydrogenchloride; sodium hydroxide; Yield given. Multistep reaction. Yields of byproduct given; 1.) water, 0-5 deg C, pH 8.5-9.5, 2.) MeOH, water, 0 deg C, pH 4.5-5;

DOI:10.1016/S0040-4039(00)87092-6

Reference yield:

→ aspartame (25548-16-7,7421-84-3)

Guidance literature:

N-CHO-L-Asparaginsaeureanhydrid, 1.)Me-CO-Et, Phe-OMe, 2.)HCl;

Reference yield: 37.0%

hydrotris(3,5-methylphenylpyrazolyl)boratozinc(II) hydroxide + aspartame (25548-16-7,7421-84-3) → [(HB(NC(CH3)CHC(C6H5)N)3)Zn(OOCCH2CH(NH2)C(O)NHCH(CH2C6H5)C(O)OCH3)]

Guidance literature:

In ethanol; dichloromethane; dipeptide (1 equiv.) in ethanol was added to soln. of Zn complex (1 equiv.) in CH2Cl2; mixt. was stirred for 40 h; solvent removed (vac.); recrystd. (n-heptane/CH2Cl2); elem. anal.;

DOI:10.1016/S0020-1693(02)00748-X

upstream raw materials:

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

L-aspartic acid N-thiocarboxyanhydride

Downstream raw materials:

3-Hydroxy-N-((S)-1-methoxycarbonyl-2-phenyl-ethyl)-succinamic acid

3-Hydroxy-N-((S)-1-methoxycarbonyl-2-phenyl-ethyl)-succinamic acid

Refernces

• 1、 Vinick, Fredic J.,Jung, Stanley. "A SUPERIOR SYNTHESIS OF ASPARTAME". . p. 1315 - 1318. Retrieved 2007/10/02.