(R)-tert-butyl-N-<(3-benzyloxycarbonyl-5-oxo-4-oxazolidinyl)-methyl>carbamate

Base Information

• Chemical Name: (R)-tert-butyl-N-<(3-benzyloxycarbonyl-5-oxo-4-oxazolidinyl)-methyl>carbamate
• CAS No.: 173259-63-7
• Molecular Formula: C₁₇H₂₂N₂O₆
• Molecular Weight: 350.371
• Mol file: 173259-63-7.mol

Synonyms:(R)-tert-butyl-N-<(3-benzyloxycarbonyl-5-oxo-4-oxazolidinyl)-methyl>carbamate

Chemical Property of (R)-tert-butyl-N-<(3-benzyloxycarbonyl-5-oxo-4-oxazolidinyl)-methyl>carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-tert-butyl-N-<(3-benzyloxycarbonyl-5-oxo-4-oxazolidinyl)-methyl>carbamate

There total 1 articles about (R)-tert-butyl-N-<(3-benzyloxycarbonyl-5-oxo-4-oxazolidinyl)-methyl>carbamate 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:

(R)-3-benzyloxycarbonyl-5-oxo-4-oxazolidinoneacetic acid (135841-16-6) + tert-butyl alcohol (75-65-0) → (R)-tert-butyl-N-<(3-benzyloxycarbonyl-5-oxo-4-oxazolidinyl)-methyl>carbamate (173259-63-7)

Guidance literature:

With diphenylphosphoranyl azide; tin(IV) chloride; triethylamine; Yield given. Multistep reaction; 1.) 80 deg C, 2 h, toluene; 2.) 70 deg C, 0.5 h;

DOI:10.1055/s-1995-4111

Reference yield: 83.0%

(R)-tert-butyl-N-<(3-benzyloxycarbonyl-5-oxo-4-oxazolidinyl)-methyl>carbamate (173259-63-7) → Nα-benzyloxycarbonyl-Nβ-tert-butyloxycarbonyl-D-2,3-diaminopropionic acid (159002-15-0,62234-36-0)

Guidance literature:

With sodium hydroxide; In water; acetone; at 0 ℃; for 3h;

DOI:10.1055/s-1995-4111

Reference yield:

(R)-tert-butyl-N-<(3-benzyloxycarbonyl-5-oxo-4-oxazolidinyl)-methyl>carbamate (173259-63-7) → (R)-2-benzyloxycarbonylamino-3-tert-butoxycarbonylaminopropanal

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / 1N NaOH / H₂O; acetone / 3 h / 0 °C

2: 1.) 1-hydroxybenzotriazole, N,N'-dicyclohexylcarbodiimide; 2.) N-methylmorpholine / 1.) CH₂Cl₂, 0 deg C, 4.5 h; 2.) CH₂Cl₂, 2 h, 0 deg C then 20 h, r.t.

3: 66 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

With 4-methyl-morpholine; sodium hydroxide; lithium aluminium tetrahydride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; water; acetone;

DOI:10.1055/s-1995-4111

upstream raw materials:

(R)-3-benzyloxycarbonyl-5-oxo-4-oxazolidinoneacetic acid

tert-butyl alcohol

Downstream raw materials:

N^α-benzyloxycarbonyl-N^β-tert-butyloxycarbonyl-D-2,3-diaminopropionic acid

(R)-2-benzyloxycarbonylamino-3-tert-butoxycarbonylamino-N-methoxy-N-methylpropanamide