(4S,5S,1'S)-4-benzyl-5-<1-<<(tert-butyloxy)carbonyl>amino>-2-phenylethyl>oxazolidin-2-one

Base Information

• Chemical Name: (4S,5S,1'S)-4-benzyl-5-<1-<<(tert-butyloxy)carbonyl>amino>-2-phenylethyl>oxazolidin-2-one
• CAS No.: 143747-10-8
• Molecular Formula: C₂₃H₂₈N₂O₄
• Molecular Weight: 396.486
• Mol file: 143747-10-8.mol

Synonyms:(4S,5S,1'S)-4-benzyl-5-<1-<<(tert-butyloxy)carbonyl>amino>-2-phenylethyl>oxazolidin-2-one

Chemical Property of (4S,5S,1'S)-4-benzyl-5-<1-<<(tert-butyloxy)carbonyl>amino>-2-phenylethyl>oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S,1'S)-4-benzyl-5-<1-<<(tert-butyloxy)carbonyl>amino>-2-phenylethyl>oxazolidin-2-one

There total 5 articles about (4S,5S,1'S)-4-benzyl-5-<1-<<(tert-butyloxy)carbonyl>amino>-2-phenylethyl>oxazolidin-2-one 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: 37.0%

phosgene (75-44-5) + (2S,3S,4S)-2-amino-4-<<(tert-butyloxy)carbonyl>amino>-1,5-diphenyl-3-hydroxypentane (134804-71-0,143838-06-6,143838-07-7,144240-04-0) → (4S,5S,1'S)-4-benzyl-5-<1-<<(tert-butyloxy)carbonyl>amino>-2-phenylethyl>oxazolidin-2-one (143747-10-8)

Guidance literature:

With 4-methyl-morpholine; In dichloromethane; toluene; at 0 ℃; for 0.5h;

DOI:10.1021/jo00047a023

Reference yield:

trans-(2S)-2-<<(tert-butyloxy)carbonyl>amino>-1,5-diphenylpent-3-ene (143747-02-8) → (4S,5S,1'S)-4-benzyl-5-<1-<<(tert-butyloxy)carbonyl>amino>-2-phenylethyl>oxazolidin-2-one (143747-10-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 76 percent / NaHCO₃, m-chloroperbenzoic acid / CH₂Cl₂ / 3 h / 5 °C

2: 91 percent / LiN₃, NH₄Cl / dimethylformamide; H₂O / 32 h / 70 °C

3: 70 percent / ammonium formate / 10percent Pd/C / methanol / 2.5 h / Ambient temperature

4: 37 percent / 4-methylmorpholine / CH₂Cl₂; toluene / 0.5 h / 0 °C

With 4-methyl-morpholine; lithium azide; ammonium formate; sodium hydrogencarbonate; ammonium chloride; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00047a023

Reference yield:

[(S)-1-(3-Benzyl-oxiranyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester (134806-56-7,143838-02-2,143838-03-3) → (4S,5S,1'S)-4-benzyl-5-<1-<<(tert-butyloxy)carbonyl>amino>-2-phenylethyl>oxazolidin-2-one (143747-10-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / LiN₃, NH₄Cl / dimethylformamide; H₂O / 32 h / 70 °C

2: 70 percent / ammonium formate / 10percent Pd/C / methanol / 2.5 h / Ambient temperature

3: 37 percent / 4-methylmorpholine / CH₂Cl₂; toluene / 0.5 h / 0 °C

With 4-methyl-morpholine; lithium azide; ammonium formate; ammonium chloride; palladium on activated charcoal; In methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00047a023

upstream raw materials:

phosgene

(2S,3S,4S)-2-amino-4-<<(tert-butyloxy)carbonyl>amino>-1,5-diphenyl-3-hydroxypentane

trans-(2S)-2-<<(tert-butyloxy)carbonyl>amino>-1,5-diphenylpent-3-ene

[(S)-1-(3-Benzyl-oxiranyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester

Downstream raw materials:

(4S,5S,1'S)-5-(1-amino-2-phenylethyl)-4-benzyloxazolidin-2-one