N-(L-alanyl)-(2S)-2-phenylglycine tert-butyl ester

Base Information

• Chemical Name: N-(L-alanyl)-(2S)-2-phenylglycine tert-butyl ester
• CAS No.: 327052-53-9
• Molecular Formula: C₁₅H₂₂N₂O₃
• Molecular Weight: 278.351
• Mol file: 327052-53-9.mol

Synonyms:N-(L-alanyl)-(2S)-2-phenylglycine tert-butyl ester

Chemical Property of N-(L-alanyl)-(2S)-2-phenylglycine tert-butyl ester

Chemical Property:

• Boiling Point: 431.1±40.0 °C(Predicted)
• PKA: 13.23±0.46(Predicted)
• Density: 1.104±0.06 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-(L-alanyl)-(2S)-2-phenylglycine tert-butyl ester

There total 5 articles about N-(L-alanyl)-(2S)-2-phenylglycine tert-butyl 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: 99.0%

L-alanin (56-41-7,25191-17-7,18875-37-1) + (S)-2-amino-2-phenylacetic acid tert-butyl ester (53934-78-4,65715-93-7,67672-72-4,124619-74-5) → N-(L-alanyl)-(2S)-2-phenylglycine tert-butyl ester (327052-53-9)

Guidance literature:

L-alanin; With 1H-imidazole; tris[(1,1,1,3,3,3-hexafluoropropan-2-yl)oxy]silane; cesium fluoride; In chloroform; at 30 ℃; for 1h; Inert atmosphere; Sealed tube;

With N-methyl-N-tert-butyldimethylsilyl-1,1,1-trifluoroacetamide; In chloroform; at 30 ℃; for 1h; Inert atmosphere; Sealed tube;

(S)-2-amino-2-phenylacetic acid tert-butyl ester; In chloroform; at 30 ℃; for 20h; Inert atmosphere; Sealed tube;

DOI:10.1021/jacs.1c02600

Reference yield: 96.0%

N-(N-carbobenzyloxy-L-alanyl)-(2S)-2-phenylglycine tert-butyl ester (860013-16-7) → N-(L-alanyl)-(2S)-2-phenylglycine tert-butyl ester (327052-53-9)

Guidance literature:

With hydrogen; palladium dihydroxide; In methanol; at 20 ℃;

DOI:10.1039/b504988a

Reference yield:

tert-butyl (S)-2-amino-2-phenylacetate hydrochloride → N-(L-alanyl)-(2S)-2-phenylglycine tert-butyl ester (327052-53-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 3.70 g / BOP; ethyldiisopropylamine / CH₂Cl₂ / 20 °C

2: 96 percent / H₂ / Pd(OH)2 on activated charcoal / methanol / 20 °C

With hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; palladium hydroxide - carbon; In methanol; dichloromethane;

DOI:10.1071/CH05102

upstream raw materials:

N-(N-carbobenzyloxy-L-alanyl)-(2S)-2-phenylglycine tert-butyl ester

(S)-2-phenylglycine

(S)-2-amino-2-phenylacetic acid tert-butyl ester

L-alanin

Downstream raw materials:

6-[(S)-2-((S)-2-tert-Butoxycarbonylamino-propionylamino)-2-phenyl-acetylamino]-hexanoic acid (S)-2-((R)-3,4-bis-benzyloxy-5-oxo-2,5-dihydro-furan-2-yl)-2-hydroxy-ethyl ester

N-[N-(tert-butyloxycarbonyl)-L-alanyl]-(2S)-2-phenylglycine

((S)-tert-butyl 2-((S)-2-(2-(3,5-difluorophenyl)acetamido)propanamido)-2-phenylacetate)

Refernces

• 1、 Abraham, Ciby J.,Paull, Daniel H.,Bekele, Tefsit,Scerba, Michael T.,Dudding, Travis,Lectka, Thomas. "A surprising mechanistic "switch" in Lewis acid activation: A bifunctional, asymmetric approach to α-hydroxy acid derivatives". scheme or table. p. 17085 - 17094. Retrieved 2009/04/13.
• 2、 Pietrancosta, Nicolas,Quelever, Gilles,Laras, Younes,Garino, Cedrik,Burlet, Stephane,Kraus, Jean Louis. "Design of β-secretase inhibitors by introduction of a mandelyl moiety in DAPT analogues". . p. 585 - 594. Retrieved 2007/10/03.