2(R)-[3(S)-(N-tert-butoxycarbonylamino)-2(R,S)-hydroxy-4-phenylbutyryl-amino]-3-phenylpropionic acid methyl ester

Base Information

• Chemical Name: 2(R)-[3(S)-(N-tert-butoxycarbonylamino)-2(R,S)-hydroxy-4-phenylbutyryl-amino]-3-phenylpropionic acid methyl ester
• CAS No.: 648433-87-8
• Molecular Formula: C₂₅H₃₂N₂O₆
• Molecular Weight: 456.539
• Mol file: 648433-87-8.mol

Synonyms:2(R)-[3(S)-(N-tert-butoxycarbonylamino)-2(R,S)-hydroxy-4-phenylbutyryl-amino]-3-phenylpropionic acid methyl ester

Chemical Property of 2(R)-[3(S)-(N-tert-butoxycarbonylamino)-2(R,S)-hydroxy-4-phenylbutyryl-amino]-3-phenylpropionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2(R)-[3(S)-(N-tert-butoxycarbonylamino)-2(R,S)-hydroxy-4-phenylbutyryl-amino]-3-phenylpropionic acid methyl ester

There total 1 articles about 2(R)-[3(S)-(N-tert-butoxycarbonylamino)-2(R,S)-hydroxy-4-phenylbutyryl-amino]-3-phenylpropionic acid methyl 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: 87.0%

D-phenylalanine methyl ester hydrochloride (13033-84-6) + 3(S)-(N-tert-butoxycarbonylamino)-2(R,S)-hydroxy-4-phenylbutyric acid (191849-93-1) → 2(R)-[3(S)-(N-tert-butoxycarbonylamino)-2(R,S)-hydroxy-4-phenylbutyryl-amino]-3-phenylpropionic acid methyl ester (648433-87-8)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/jm0301336

Reference yield:

2(R)-[3(S)-(N-tert-butoxycarbonylamino)-2(R,S)-hydroxy-4-phenylbutyryl-amino]-3-phenylpropionic acid methyl ester (648433-87-8) → (R)-2-((S)-3-Amino-2-hydroxy-4-phenyl-butyrylamino)-3-phenyl-propionic acid methyl ester

Guidance literature:

With hydrogenchloride; In 1,4-dioxane;

DOI:10.1021/jm0301336

Reference yield:

2(R)-[3(S)-(N-tert-butoxycarbonylamino)-2(R,S)-hydroxy-4-phenylbutyryl-amino]-3-phenylpropionic acid methyl ester (648433-87-8) → (S)-2-[(S)-3-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-2-oxo-4-phenyl-butyrylamino]-3-phenyl-propionic acid methyl ester

Guidance literature:

Multi-step reaction with 5 steps

1: HCl / dioxane

2: 73 percent / EDC; HOBT; NMM / dimethylformamide / 20 °C

3: 79 percent / Dess-Martin reagent / CH₂Cl₂ / 4 h / 20 °C

4: 76 percent / EDC; HOBT; NMM / dimethylformamide / 20 °C

5: 95 percent / Dess-Martin reagent / CH₂Cl₂ / 4 h / 20 °C

With 4-methyl-morpholine; hydrogenchloride; benzotriazol-1-ol; Dess-Martin periodane; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm0301336

upstream raw materials:

D-phenylalanine methyl ester hydrochloride

3(S)-(N-tert-butoxycarbonylamino)-2(R,S)-hydroxy-4-phenylbutyric acid

Downstream raw materials:

2(S)-[3(S)-(N-Cbz-L-leucylamino)-2(R,S)-hydroxy-4-phenylbutyryl-amino]-3-phenylpropionic acid methyl ester

2(R)-[3(S)-(N-Cbz-L-leucylamino)-2(R,S)-hydroxy-4-phenylbutyryl-amino]-3-phenylpropionic acid methyl ester

(R)-2-[(S)-3-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-2-oxo-4-phenyl-butyrylamino]-3-phenyl-propionic acid methyl ester