N-acetyl-α-(D)-phenylglycine ethyl ester

Base Information

• Chemical Name: N-acetyl-α-(D)-phenylglycine ethyl ester
• CAS No.: 14190-09-1
• Molecular Formula: C₁₂H₁₅NO₃
• Molecular Weight: 221.256
• Mol file: 14190-09-1.mol

Synonyms:N-acetyl-α-(D)-phenylglycine ethyl ester

Chemical Property of N-acetyl-α-(D)-phenylglycine ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-acetyl-α-(D)-phenylglycine ethyl ester

There total 9 articles about N-acetyl-α-(D)-phenylglycine ethyl 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:

2-Methyl-5-oxo-4-phenyl-4,5-dihydro-oxazole-4-carboxylic acid ethyl ester (162247-66-7) → N-acetyl-α-(D)-phenylglycine ethyl ester (14190-09-1) + (S)-N-acetyl-2-phenylglycine (14257-84-2,15962-46-6,29633-99-6,42429-20-9) + N-acetyl-α-(L)-phenylglycine ethyl ester

Guidance literature:

With water; at 100 ℃; Yield given. Yields of byproduct given;

Reference yield:

N-tert-butanesulfinylphenylglycine ethyl ester + acetic anhydride (108-24-7) → N-acetyl-α-(D)-phenylglycine ethyl ester (14190-09-1) + N-acetyl-α-(L)-phenylglycine ethyl ester

Guidance literature:

N-tert-butanesulfinylphenylglycine ethyl ester; With hydrogenchloride; In 1,4-dioxane; at 20 ℃; for 3h;

acetic anhydride; With N,N-diethyl-N-isopropylamine; In dichloromethane; at 20 ℃; for 1h; Further stages. Title compound not separated from byproducts.;

DOI:10.1021/ol0711220

Reference yield:

N-Acetyl-α-phenylglycine ethyl ester (14304-68-8) → N-acetyl-α-(D)-phenylglycine ethyl ester (14190-09-1) + N-acetyl-α-(L)-phenylglycine ethyl ester

Guidance literature:

With water; In ethanol; at 25 ℃; for 96h; optical yield given as %ee; enantioselective reaction; Microbiological reaction; Resolution of racemate;

DOI:10.1016/j.tetasy.2010.02.011

upstream raw materials:

phenyllead(IV) triacetate

4-Ethoxycarbonyl-2-methyl-4,5-dihydro-1,3-oxazol-5-one

2-Methyl-5-oxo-4-phenyl-4,5-dihydro-oxazole-4-carboxylic acid ethyl ester

acetic anhydride

Refernces

• 1、 Stella, Selvaraj,Chadha, Anju. "Resolution of N-protected amino acid esters using whole cells of Candida parapsilosis ATCC 7330". experimental part. p. 457 - 460. Retrieved 2010/06/21.
• 2、 Morgan, Jacqueline,Pinhey, John T.,Sherry, Christopher J.. "Reaction of organolead triacetates with 4-ethoxycarbonyl-2-methyl-4,5-dihydro-1,3-oxazol-5-one. The synthesis of α-aryl- and α-vinyl-N-acetylglycines and their ethyl esters and their enzymic resolution". . p. 613 - 619. Retrieved 2007/10/03.