methyl (2R,3R)-2-(benzoylamino)-3-hydroxy-3-phenylpropanoate

Base Information

• Chemical Name: methyl (2R,3R)-2-(benzoylamino)-3-hydroxy-3-phenylpropanoate
• CAS No.: 1104494-04-3
• Molecular Formula: C₁₇H₁₇NO₄
• Molecular Weight: 299.326
• Mol file: 1104494-04-3.mol

Synonyms:methyl (2R,3R)-2-(benzoylamino)-3-hydroxy-3-phenylpropanoate

Chemical Property of methyl (2R,3R)-2-(benzoylamino)-3-hydroxy-3-phenylpropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2R,3R)-2-(benzoylamino)-3-hydroxy-3-phenylpropanoate

There total 10 articles about methyl (2R,3R)-2-(benzoylamino)-3-hydroxy-3-phenylpropanoate 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: 79.0%

benzoyl chloride (98-88-4) + α-Phenylacyl amino acid methyl ester hydrochloride (38061-23-3,81202-39-3) → methyl (2S,3S)-2-benzoylamino-3-hydroxy-3-phenylpropionate + methyl (2R,3R)-2-(benzoylamino)-3-hydroxy-3-phenylpropanoate (1104494-04-3)

Guidance literature:

α-Phenylacyl amino acid methyl ester hydrochloride; With hydrogen; sodium acetate; bis(1,5-cyclooctadiene)diiridium(I) dichloride; (S)-(-)-(6,6’-dimethoxybiphenyl-2,2’-diyl)bis(diphenylphosphine); In dichloromethane; acetic acid; at 20 ℃; for 3.16h; under 76005.1 Torr;

With hydrogenchloride; In water;

benzoyl chloride; With triethylamine; In tetrahydrofuran; at 0 - 20 ℃; for 1h; Product distribution / selectivity;

Reference yield:

C10H13NO3*ClH + benzoyl chloride (98-88-4) → methyl (2R,3R)-2-(benzoylamino)-3-hydroxy-3-phenylpropanoate (1104494-04-3)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 2.5h; Inert atmosphere;

DOI:10.1039/c5ra10385a

Reference yield:

benzoic acid anhydride (93-97-0) + α-Phenylacyl amino acid methyl ester hydrochloride (38061-23-3,81202-39-3) → methyl (2S,3S)-2-benzoylamino-3-hydroxy-3-phenylpropionate + methyl (2S,3R)-2-benzoylamino-3-hydroxy-3-phenylpropionate + methyl (2R,3R)-2-(benzoylamino)-3-hydroxy-3-phenylpropanoate (1104494-04-3) + methyl (2R,3S)-2-benzoylamino-3-hydroxy-3-phenylpropionate (19185-84-3,19185-85-4)

Guidance literature:

α-Phenylacyl amino acid methyl ester hydrochloride; With hydrogen; sodium acetate; acetic acid; chiral ferrocene-based rhodium; at 23 ℃; for 0.5h; under 38000 Torr;

benzoic acid anhydride; With triethylamine; In tetrahydrofuran; at 0 - 23 ℃; Title compound not separated from byproducts;

DOI:10.1016/j.tetasy.2006.01.040

upstream raw materials:

benzoyl chloride

α-Phenylacyl amino acid methyl ester hydrochloride

benzoic acid anhydride

methyl (2R,3R)-2-amino-3-hydroxy-3-phenylpropionate