(betaR)-N-Benzoyl-beta-methyl-L-phenylalanine methyl ester

Base Information

• Chemical Name: (betaR)-N-Benzoyl-beta-methyl-L-phenylalanine methyl ester
• CAS No.: 256442-52-1
• Molecular Formula: C₁₈H₁₉NO₃
• Molecular Weight: 297.354
• DSSTox Substance ID: DTXSID801218066
• Nikkaji Number: J1.996.215F
• Mol file: 256442-52-1.mol

Synonyms:CIS-(2S,3R)-METHYL 2-BENZAMIDO-3-PHENYLBUTANOATE;SCHEMBL22303089;DTXSID801218066;MFCD31803384;256442-52-1;(betaR)-N-Benzoyl-beta-methyl-L-phenylalanine methyl ester

Chemical Property of (betaR)-N-Benzoyl-beta-methyl-L-phenylalanine methyl ester

Chemical Property:

• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 297.13649347
• Heavy Atom Count: 22
• Complexity: 371

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C1=CC=CC=C1)C(C(=O)OC)NC(=O)C2=CC=CC=C2
• Isomeric SMILES: C[C@H](C1=CC=CC=C1)[C@@H](C(=O)OC)NC(=O)C2=CC=CC=C2

Technology Process of (betaR)-N-Benzoyl-beta-methyl-L-phenylalanine methyl ester

There total 11 articles about (betaR)-N-Benzoyl-beta-methyl-L-phenylalanine methyl ester 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: 80.0%

(Z)-N-benzoyl-β-methyldidehydrophenylalanine methyl ester (89141-16-2) → methyl (2R,3S)-2-benzamide-3-phenylbutanoate (256442-53-2) + methyl (2S,3R)-2-benzamide-3-phenylbutanoate (256442-52-1)

Guidance literature:

With hydrogen; bis(cycloocta-1,5-diene)rhodium(I) trifluoromethanesulfonate; (S,S)-iPr-CnrPHOS; In dichloromethane; benzene; at 20 ℃; for 20h; under 75006 Torr;

DOI:10.1016/S0040-4039(99)01767-0

Reference yield: 49.0%

C18H17NO3 → methyl (2R,3S)-2-benzamide-3-phenylbutanoate (256442-53-2) + methyl (2S,3R)-2-benzamide-3-phenylbutanoate (256442-52-1)

Guidance literature:

With palladium on activated charcoal; hydrogen; In methanol; at 35 ℃; for 12h; under 2585.81 Torr;

Reference yield:

Hippuric Acid (495-69-2,140480-84-8,21251-67-2,91787-63-2,66407-11-2) → methyl (2S,3R)-2-benzamide-3-phenylbutanoate (256442-52-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 38 percent / acetic anhydride; lead(IV) acetate / tetrahydrofuran / 24 h / Heating

2: 95 percent / methanol / 0.5 h / 20 °C

3: 96 percent / H₂ / Pd/C / ethyl acetate / 6 h / 30 °C

4: amylose 10-undecenoate/3,5-di(Me)phenylcarbamate on AllSiO₂ / hexane; propan-2-ol; CHCl₃ / 4.4 h / 25 °C

With lead(IV) acetate; 3,5-dimethylphenyl carbamate; amylose 10-undecenoate; hydrogen; acetic anhydride; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; chloroform; ethyl acetate; isopropyl alcohol;

DOI:10.1016/j.tet.2003.11.044

upstream raw materials:

(Z)-N-benzoyl-β-methyldidehydrophenylalanine methyl ester

Hippuric Acid

(Z)-2-phenyl-4-(α-phenylethylidene)-5-(4H)-oxazolone

acetophenone

Downstream raw materials:

threo-L-(2S,3R)-β-methylphenylalanine