(S)-2-{(S)-2-tert-Butoxycarbonylamino-3-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-propionylamino}-3-phenyl-propionic acid benzyl ester

Base Information

• Chemical Name: (S)-2-{(S)-2-tert-Butoxycarbonylamino-3-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-propionylamino}-3-phenyl-propionic acid benzyl ester
• CAS No.: 181213-26-3
• Molecular Formula: C₃₄H₃₈N₄O₇S
• Molecular Weight: 646.764
• Mol file: 181213-26-3.mol

Synonyms:

Chemical Property of (S)-2-{(S)-2-tert-Butoxycarbonylamino-3-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-propionylamino}-3-phenyl-propionic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-{(S)-2-tert-Butoxycarbonylamino-3-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-propionylamino}-3-phenyl-propionic acid benzyl ester

There total 1 articles about (S)-2-{(S)-2-tert-Butoxycarbonylamino-3-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-propionylamino}-3-phenyl-propionic acid benzyl 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: 65.0%

L-phenylalanine benzyl ester p-toluene-sulfonic acid salt (1738-78-9) + Boc-His(Tos)-OH (35899-43-5) → (S)-2-{(S)-2-tert-Butoxycarbonylamino-3-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-propionylamino}-3-phenyl-propionic acid benzyl ester (181213-26-3)

Guidance literature:

With potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1.) Et₂O, 2.) DMF, RT, overnight;

DOI:10.1016/0968-0896(96)00085-5

Reference yield:

(S)-2-{(S)-2-tert-Butoxycarbonylamino-3-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-propionylamino}-3-phenyl-propionic acid benzyl ester (181213-26-3) → (2R,3R)-2,3-Diacetoxy-N-{(S)-1-((S)-1-benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-2-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-ethyl}-succinamic acid

Guidance literature:

Multi-step reaction with 2 steps

1: TFA / 0.67 h / Ambient temperature

2: CH₂Cl₂ / 3.5 h / 0 - 20 °C

With trifluoroacetic acid; In dichloromethane;

DOI:10.1016/0968-0896(96)00085-5

Reference yield:

(S)-2-{(S)-2-tert-Butoxycarbonylamino-3-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-propionylamino}-3-phenyl-propionic acid benzyl ester (181213-26-3) → (2R,3R)-2,3-Diacetoxy-N-{(S)-1-((S)-1-benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-2-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-ethyl}-succinamic acid methyl ester (181213-27-4)

Guidance literature:

Multi-step reaction with 3 steps

1: TFA / 0.67 h / Ambient temperature

2: CH₂Cl₂ / 3.5 h / 0 - 20 °C

3: diethyl ether / 0 °C

With trifluoroacetic acid; In diethyl ether; dichloromethane;

DOI:10.1016/0968-0896(96)00085-5

upstream raw materials:

L-phenylalanine benzyl ester p-toluene-sulfonic acid salt

Boc-His(Tos)-OH

Downstream raw materials:

(2R,3R)-2,3-Diacetoxy-N-{(S)-1-((S)-1-benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-2-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-ethyl}-succinamic acid methyl ester