3-oxo-(4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanoic acid ethyl ester

Base Information

• Chemical Name: 3-oxo-(4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanoic acid ethyl ester
• CAS No.: 112151-92-5
• Molecular Formula: C₁₈H₃₁NO₅
• Molecular Weight: 341.448
• Mol file: 112151-92-5.mol

Synonyms:3-oxo-(4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanoic acid ethyl ester

Chemical Property of 3-oxo-(4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-oxo-(4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanoic acid ethyl ester

There total 4 articles about 3-oxo-(4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanoic acid ethyl 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:

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → 3-oxo-(4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanoic acid ethyl ester (112151-92-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / H₂, acetic acid / PtO₂ / H₂O / 18 h / 50 °C / 2327.2 Torr

2: 100 percent / 0.5 N aq. NaOH / dioxane / 1.) from 0deg C to RT, 3 h, 2.) RT, 17 h

3: 1.) N,N'-carbonyldiimidazole / 1.) THF, RT, 20 h, 2.) RT, 3.5 h

With sodium hydroxide; hydrogen; acetic acid; 1,1'-carbonyldiimidazole; platinum(IV) oxide; In 1,4-dioxane; water;

DOI:10.1021/jo00239a036

Reference yield:

L-cyclohexylalanine (27527-05-5) → 3-oxo-(4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanoic acid ethyl ester (112151-92-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / 0.5 N aq. NaOH / dioxane / 1.) from 0deg C to RT, 3 h, 2.) RT, 17 h

2: 1.) N,N'-carbonyldiimidazole / 1.) THF, RT, 20 h, 2.) RT, 3.5 h

With sodium hydroxide; 1,1'-carbonyldiimidazole; In 1,4-dioxane;

DOI:10.1021/jo00239a036

Reference yield:

(S)-2-tert-butoxycarbonylamino-3-cyclohexylpropionic acid (37736-82-6) + Dibasic magnesium salt of ethyl hydrogen malonate (35116-15-5) → 3-oxo-(4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanoic acid ethyl ester (112151-92-5)

Guidance literature:

With 1,1'-carbonyldiimidazole; Yield given. Multistep reaction; 1.) THF, RT, 20 h, 2.) RT, 3.5 h;

DOI:10.1021/jo00239a036

upstream raw materials:

(S)-2-tert-butoxycarbonylamino-3-cyclohexylpropionic acid

Dibasic magnesium salt of ethyl hydrogen malonate

(S)-4-tert-Butoxycarbonylamino-5-cyclohexyl-3-hydroxy-pentanoic acid ethyl ester

L-phenylalanine

Downstream raw materials:

(3S)-3-hydroxy-(4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanoic acid ethyl ester

(3R)-3-hydroxy-(4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanoic acid ethyl ester

(3R,4R)-4-tert-Butoxycarbonylamino-5-cyclohexyl-3-hydroxy-pentanoic acid ethyl ester

(3S,4R)-4-[(tert-butyloxycarbonyl)amino]-5-cyclohexyl-3-hydroxypentanoic acid ethyl ester

Refernces

• 1、 Nishi, T.,Kitamura, M.,Ohkuma, T.,Noyori, R.. "SYNTHESIS OF ASATINE AND ITS ANALOGUES BY HOMOGENEOUS ASYMMETRIC HYDROGENATION". . p. 6327 - 6330. Retrieved 2007/10/02.