(S)-2,2-dimethyl-4-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid benzyl ester

Base Information

• Chemical Name: (S)-2,2-dimethyl-4-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid benzyl ester
• CAS No.: 607376-67-0
• Molecular Formula: C₁₅H₁₉NO₄
• Molecular Weight: 277.32
• Mol file: 607376-67-0.mol

Synonyms:(S)-2,2-dimethyl-4-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid benzyl ester

Chemical Property of (S)-2,2-dimethyl-4-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2,2-dimethyl-4-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid benzyl ester

There total 11 articles about (S)-2,2-dimethyl-4-(2-oxo-ethyl)-oxazolidine-3-carboxylic 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: 98.0%

2-[(4S)-(3-benzyloxycarbonyl-2,2-dimethyl-1,3-oxazolidin-4-y)]ethanol (607376-66-9) → (S)-2,2-dimethyl-4-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid benzyl ester (607376-67-0)

Guidance literature:

2-[(4S)-(3-benzyloxycarbonyl-2,2-dimethyl-1,3-oxazolidin-4-y)]ethanol; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -70 ℃;

With triethylamine; In dichloromethane; Cooling;

Reference yield:

[(1S)-3-hydroxy-1-(hydroxymethyl)propyl]carbamic acid phenylmethyl ester (118219-23-1) → (S)-2,2-dimethyl-4-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid benzyl ester (607376-67-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: toluene-4-sulfonic acid / 2 h / 20 °C

1.2: 72 h

1.3: 64 h / 20 °C

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -70 °C

2.2: -70 °C

With oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; In dichloromethane;

Reference yield:

N-(benzyloxycarbonyl)-L-aspartic acid 4-methyl ester (3160-47-2) → (S)-2,2-dimethyl-4-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid benzyl ester (607376-67-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: HOBt; DCC / tetrahydrofuran / 0.5 h / 0 °C

1.2: 86 percent / NaBH₄ / tetrahydrofuran / 0.5 h / 0 °C

2.1: 87 percent / p-toluenesulfonic acid hydrate / acetone / 20 °C

3.1: 91 percent / NaBH₄; CaCl₂ / ethanol / 0 °C

4.1: SO₃*pyridine; Et₃N / CHCl₃; dimethylsulfoxide / 1 h / 0 °C

With sodium tetrahydroborate; pyridine-SO₃ complex; benzotriazol-1-ol; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; calcium chloride; In tetrahydrofuran; ethanol; chloroform; dimethyl sulfoxide; acetone;

DOI:10.3987/COM-04-10206

upstream raw materials:

2-[(4S)-(3-benzyloxycarbonyl-2,2-dimethyl-1,3-oxazolidin-4-y)]ethanol

N-(benzyloxycarbonyl)-L-aspartic acid 4-methyl ester

methyl (3S)-3-[[(benzyloxy)carbonyl]amino]-4-hydroxybutanoate

methyl (4S)-(3-benzyloxycarbonyl-2,2-dimethyl-1,3-oxazolidin-4-y)acetate

Downstream raw materials:

methyl (5S,2Z)-4-(3-benzyloxycarbonyl-2,2-dimethyl-1,3-oxazolidin-4-yl)-2-t-butoxycarbonylamino-2-butenoate

methyl 5-benzyloxycarbonylamino-6-oxo-1-hydropyridine-2-carboxylate

methyl 5-benzyloxycarbonylamino-6-methoxypyridine-2-carboxylate

methyl (5S)-5-benzyloxycarbonylamino-6-oxo-1,4,5-trihydropyridine-2-carboxylate