N-ALPHA-BENZYLOXYCARBONYL-N-ALPHA-METHYL-D-PHENYLALANINE

Base Information

• Chemical Name: N-ALPHA-BENZYLOXYCARBONYL-N-ALPHA-METHYL-D-PHENYLALANINE
• CAS No.: 114526-00-0
• Molecular Formula: C18H19 N O4
• Molecular Weight: 313.353
• Hs Code.: 2924299090
• Mol file: 114526-00-0.mol

Synonyms:N-CBZ-N-METHYL-D-PHENYLALANINE;N-ALPHA-BENZYLOXYCARBONYL-N-ALPHA-METHYL-D-PHENYLALANINE;Z-D-MEPHE-OH;CBZ-N-METHYL-D-PHENYLALANINE;N-Benzyloxycarbonyl-N-methyl-D-phenylalanine

Chemical Property of N-ALPHA-BENZYLOXYCARBONYL-N-ALPHA-METHYL-D-PHENYLALANINE

Chemical Property:

• PSA: 66.84000
• LogP: 2.95090

Purity/Quality:

98%Min ^*data from raw suppliers

Z-N-Me-D-Phe-OH 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-ALPHA-BENZYLOXYCARBONYL-N-ALPHA-METHYL-D-PHENYLALANINE

There total 5 articles about N-ALPHA-BENZYLOXYCARBONYL-N-ALPHA-METHYL-D-PHENYLALANINE 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: 97.5%

Cbz-D-Phe (2448-45-5) + methyl iodide (74-88-4) → (2R)-2-[[(benzyloxy)carbonyl](methyl)amino]-3-phenylpropanoic acid (114526-00-0)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 22h;

DOI:10.1021/jo030358o

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + Cbz-D-Phe (2448-45-5) → (2R)-2-[[(benzyloxy)carbonyl](methyl)amino]-3-phenylpropanoic acid (114526-00-0)

Guidance literature:

formaldehyd; Cbz-D-Phe; With (1S)-10-camphorsulfonic acid; In toluene; for 0.5h; Reflux; Inert atmosphere;

With triethylsilane; trifluoroacetic acid; In chloroform; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1021/ml400528y

Reference yield:

benzyl hydroxy(methyl)carbamate (15058-52-3) → (S)-N-benzyloxycarbonyl-N-methyl-phenyl alanine (2899-07-2) + (2R)-2-[[(benzyloxy)carbonyl](methyl)amino]-3-phenylpropanoic acid (114526-00-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / dichloromethane / 3 h / 0 °C

2.1: (+)-(2S)-2-(3-ethylbenzyl)-2,3-dimethylimidazolidin-4-one; 2,6-dimethylpyridinium trifluoromethanesulfonate; 2,6-dimethylpyridine / dimethyl sulfoxide; acetonitrile / 16 h

2.2: 3 h

With 2,6-dimethylpyridine; 2,6-dimethylpyridinium trifluoromethanesulfonate; (+)-(2S)-2-(3-ethylbenzyl)-2,3-dimethylimidazolidin-4-one; triethylamine; In dichloromethane; dimethyl sulfoxide; acetonitrile;

DOI:10.1021/ja406181e

upstream raw materials:

Cbz-D-Phe

methyl iodide

benzyl hydroxy(methyl)carbamate

3-phenyl-propionaldehyde

Downstream raw materials:

C₂₂H₂₇NO₄

(1R,2S)-2-[(R)-2-(Benzyloxycarbonyl-methyl-amino)-3-phenyl-propionylamino]-cyclohexanecarboxylic acid

C₃₉H₄₈N₆O₇

Refernces

• 1、 Cecere, Giuseppe,Koenig, Christian M.,Alleva, Jennifer L.,MacMillan, David W. C.. "Enantioselective direct α-amination of aldehydes via a photoredox mechanism: A strategy for asymmetric amine fragment coupling". . p. 11521 - 11524. Retrieved 2013/09/02.