L-Phenylalanine, a-methyl-N-[(phenylmethoxy)carbonyl]-

Base Information

• Chemical Name: L-Phenylalanine, a-methyl-N-[(phenylmethoxy)carbonyl]-
• CAS No.: 97206-19-4
• Molecular Formula: C18H19NO4
• Molecular Weight: 313.353
• Mol file: 97206-19-4.mol

Synonyms:(2S)-2-benzyloxycarbonylamino-2-methyl-3-phenylpropanoic acid;N-(benzyloxycarbonyl)-α-methyl-L-phenylalanine;Z-L-(αMe)Phe-OH;(S)-N-carbobenzyloxy-(α-methyl)phenylalanine;

Chemical Property of L-Phenylalanine, a-methyl-N-[(phenylmethoxy)carbonyl]-

Chemical Property:

• PSA: 75.63000
• LogP: 3.38970

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of L-Phenylalanine, a-methyl-N-[(phenylmethoxy)carbonyl]-

There total 17 articles about L-Phenylalanine, a-methyl-N-[(phenylmethoxy)carbonyl]- 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: 86.2%

(S)-2-amino-2-methyl-3-phenylpropanoic acid (23239-35-2) + benzyl chloroformate (501-53-1,94274-21-2) → (2S)-2-benzyloxycarbonylamino-2-methyl-3-phenylpropanoic acid (97206-19-4)

Guidance literature:

With sodium hydroxide; In acetone; for 12h; Ambient temperature;

DOI:10.1002/recl.19951140417

Reference yield: 64.0%

benzyl (2S,3R,5S)-5-benzyl-2,3-dimethoxy-2,3,5-trimethyl-6-oxomorpholine-4-carboxylate (565234-27-7) → (2S)-2-benzyloxycarbonylamino-2-methyl-3-phenylpropanoic acid (97206-19-4)

Guidance literature:

With trifluoroacetic acid; at 20 ℃; for 0.5h;

DOI:10.1039/b210673f

Reference yield:

Cbz-D-Phe (2448-45-5) → (2S)-2-benzyloxycarbonylamino-2-methyl-3-phenylpropanoic acid (97206-19-4)

Guidance literature:

Multi-step reaction with 3 steps

1: p-toluolsulfonic acid / 1,1,1-trichloro-ethane / 18 h / Heating

2: 1) K-hexamethyldisilazide / 1) THF-toluene, -78 deg C, 5 min, 2) warming up to rt.

3: 1N NaOH / methanol / Ambient temperature

With sodium hydroxide; K-hexamethyldisilazide; toluene-4-sulfonic acid; In methanol; 1,1,1-trichloroethane;

DOI:10.1016/S0040-4039(01)81432-5

upstream raw materials:

(2S,4S)-4-Benzyl-2-(2,4-dichloro-phenyl)-4-methyl-5-oxo-oxazolidine-3-carboxylic acid benzyl ester

(2R,4S)-4-Benzyl-2-(2,4-dichloro-phenyl)-4-methyl-5-oxo-oxazolidine-3-carboxylic acid benzyl ester

(S)-2-amino-2-methyl-3-phenylpropanoic acid

benzyl chloroformate

Downstream raw materials:

(R)-2-amino-2-methyl-3-phenylpropanoic acid

Cbz-L-(α-Me)Phe-NH-t-Bu