(S)-4-(2-Adamantan-1-yl-ethylcarbamoyl)-4-benzyloxycarbonylamino-butyric acid benzyl ester

Base Information

• Chemical Name: (S)-4-(2-Adamantan-1-yl-ethylcarbamoyl)-4-benzyloxycarbonylamino-butyric acid benzyl ester
• CAS No.: 137795-78-9
• Molecular Formula: C₃₂H₄₀N₂O₅
• Molecular Weight: 532.68
• Mol file: 137795-78-9.mol

Synonyms:(S)-4-(2-Adamantan-1-yl-ethylcarbamoyl)-4-benzyloxycarbonylamino-butyric acid benzyl ester

Chemical Property of (S)-4-(2-Adamantan-1-yl-ethylcarbamoyl)-4-benzyloxycarbonylamino-butyric acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-(2-Adamantan-1-yl-ethylcarbamoyl)-4-benzyloxycarbonylamino-butyric acid benzyl ester

There total 2 articles about (S)-4-(2-Adamantan-1-yl-ethylcarbamoyl)-4-benzyloxycarbonylamino-butyric 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:

2-(1-adamantyl)ethanamine (26482-53-1) + (2R)-5-(benzyloxy)-2-{[(benzyloxy)carbonyl]amino}-5-oxopentanoic acid (59486-73-6) → (R)-4-(2-Adamantan-1-yl-ethylcarbamoyl)-4-benzyloxycarbonylamino-butyric acid benzyl ester (137795-78-9)

Guidance literature:

With chloroformic acid ethyl ester; triethylamine; Multistep reaction; 1.) THF, -10 deg C, 15 min, 2.)a) THF, -10 deg C, 1 h, b) RT, 3 h;

DOI:10.1021/jm00079a003

Reference yield:

N-benzyloxycarbonyl-5-O-benzyl-L-glutamic acid (5680-86-4) + 2-(1-adamantyl)ethanamine (26482-53-1) → (S)-4-(2-Adamantan-1-yl-ethylcarbamoyl)-4-benzyloxycarbonylamino-butyric acid benzyl ester (137795-78-9)

Guidance literature:

With chloroformic acid ethyl ester; triethylamine; Multistep reaction; 1.) THF, -10 deg C, 15 min, 2.)a) THF, -10 deg C, 1 h, b) RT, 3 h;

DOI:10.1021/jm00079a003

Reference yield:

(S)-4-(2-Adamantan-1-yl-ethylcarbamoyl)-4-benzyloxycarbonylamino-butyric acid benzyl ester (137795-78-9) → (S)-4-(2-Adamantan-1-yl-ethylcarbamoyl)-4-(3-chloro-benzoylamino)-butyric acid (137795-63-2)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂, H₂O / 10percent Pd/activated charcoal / methanol / 2 h / 760 Torr / Ambient temperature

2: aq. NaOH / tetrahydrofuran / 3 h / Ambient temperature

With sodium hydroxide; water; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol;

DOI:10.1021/jm00079a003

upstream raw materials:

N-benzyloxycarbonyl-5-O-benzyl-L-glutamic acid

2-(1-adamantyl)ethanamine

(2R)-5-(benzyloxy)-2-{[(benzyloxy)carbonyl]amino}-5-oxopentanoic acid

Downstream raw materials:

(S)-4-(2-Adamantan-1-yl-ethylcarbamoyl)-4-(3-chloro-benzoylamino)-butyric acid

CR 2227

(R)-4-(2-Adamantan-1-yl-ethylcarbamoyl)-4-(3-chloro-benzoylamino)-butyric acid