Ethyl 2-((1S,2R)-2-hydroxy-1,2-diphenylethylamino)acetate

Base Information

• Chemical Name: Ethyl 2-((1S,2R)-2-hydroxy-1,2-diphenylethylamino)acetate
• CAS No.: 100678-82-8
• Molecular Formula: C18H21 N O3
• Molecular Weight: 299.37
• Mol file: 100678-82-8.mol

Synonyms:Glycine,N-(2-hydroxy-1,2-diphenylethyl)-, ethyl ester, [R-(R*,S*)]-

Chemical Property of Ethyl 2-((1S,2R)-2-hydroxy-1,2-diphenylethylamino)acetate

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 2.33E-08mmHg at 25°C
• Melting Point: 127-128 ºC
• Refractive Index: 1.572
• Boiling Point: 436 ºC
• Flash Point: 217.2°C
• PSA: 58.56000
• Density: 1.150
• LogP: 3.00490

Purity/Quality:

99% ^*data from raw suppliers

N-[(1S,2R)-2-Hydroxy-1,2-diphenylethyl]-glycineEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-[(1S,2R)-2-Hydroxy-1,2-diphenylethyl]-glycine Ethyl Ester is a reactant used in the preparation of α-helixes of BCL-2 domains and collagen cross-linking agents such as (5S,5’S)-Dihydroxy Lysinonorleucine (D452900).

Technology Process of Ethyl 2-((1S,2R)-2-hydroxy-1,2-diphenylethylamino)acetate

There total 5 articles about Ethyl 2-((1S,2R)-2-hydroxy-1,2-diphenylethylamino)acetate 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: 98.0%

(1R,2S)-2-Amino-1,2-diphenylethanol (23190-16-1) + ethyl bromoacetate (105-36-2) → 2-((1S,2R)-2-hydroxy-1,2-diphenylethylamino)acetic acid ethyl ester (100678-82-8)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 20 ℃; for 18h;

DOI:10.1039/c3cc45231j

Reference yield:

erythro-2-amino-1,2-diphenylethanol (530-36-9,3764-63-4,13286-63-0,23190-16-1,23190-17-2,23364-44-5,23412-95-5,39664-87-4,88082-66-0) → 2-((1S,2R)-2-hydroxy-1,2-diphenylethylamino)acetic acid ethyl ester (100678-82-8)

Guidance literature:

Multi-step reaction with 2 steps

2: Et₃N / tetrahydrofuran / 25 °C

With triethylamine; In tetrahydrofuran;

DOI:10.1021/ja00265a053

Reference yield:

2-amino-1,2-diphenylethanol (530-36-9,3764-63-4,13286-63-0,23190-16-1,23190-17-2,23364-44-5,23412-95-5,39664-87-4,88082-66-0) → 2-((1S,2R)-2-hydroxy-1,2-diphenylethylamino)acetic acid ethyl ester (100678-82-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: L-glutamic acid / ethanol / 72 °C

1.2: 90 °C

2.1: triethylamine / tetrahydrofuran / 20 °C

With L-glutamic acid; triethylamine; In tetrahydrofuran; ethanol;

upstream raw materials:

(1R,2S)-2-Amino-1,2-diphenylethanol

ethyl bromoacetate

erythro-2-amino-1,2-diphenylethanol

2-amino-1,2-diphenylethanol

Downstream raw materials:

(3S,5S,6R)-4-(tert-butyloxycarbonyl)-5,6-diphenyl-3-methyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

(3S,5S,6R)-tert-butyl 3-methyl-2-oxo-3-(pent-4-enyl)-5,6-diphenylmorpholine-4-carboxylate

tert-butyl (2R,3S)-6-oxo-2,3-diphenylmorpholine-4-carboxylate

(3R,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-<2'-oxo-2'-(4-methoxyphenyl)ethyl>-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

Refernces

• 1、 Yeo, David J.,Warriner, Stuart L.,Wilson, Andrew J.. "Monosubstituted alkenyl amino acids for peptide "stapling"". supporting information. p. 9131 - 9133. Retrieved 2013/09/24.
• 2、 Williams, Robert M.,Sinclair, Peter J.,DeMong, Duane E.,Chen, Daimo,Zhai, Dongguan. "Asymmetric synthesis of N-tert-butoxycarbonyl α- Amino acids. synthesis of (5S,6R)-4-tert-butoxycarbonyl-5,6-diphenylmorpholin-2-ONE [(4-Morpholinecarboxylic acid, 6-oxo-2,3-diphenyl-, 1,1-dimethylethyl ester, (2S,3R)-)]". . p. 18 - 30. Retrieved 2017/09/19.