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

Base Information

• Chemical Name: (R)-2-benzyloxycarbonylamino-3-tert-butoxycarbonylamino-N-methoxy-N-methylpropanamide
• CAS No.: 173259-64-8
• Molecular Formula: C₁₈H₂₇N₃O₆
• Molecular Weight: 381.429
• Mol file: 173259-64-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about (R)-2-benzyloxycarbonylamino-3-tert-butoxycarbonylamino-N-methoxy-N-methylpropanamide 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) → (R)-2-benzyloxycarbonylamino-3-tert-butoxycarbonylamino-N-methoxy-N-methylpropanamide (173259-64-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) diphenylphosphoryl azide, Et₃N; 2.) SnCl₄ / 1.) 80 deg C, 2 h, toluene; 2.) 70 deg C, 0.5 h

2: 83 percent / 1N NaOH / H₂O; acetone / 3 h / 0 °C

3: 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.

With 4-methyl-morpholine; sodium hydroxide; diphenylphosphoranyl azide; tin(IV) chloride; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In water; acetone;

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-butoxycarbonylamino-N-methoxy-N-methylpropanamide (173259-64-8)

Guidance literature:

Multi-step reaction with 2 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.

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

DOI:10.1055/s-1995-4111

Reference yield:

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + Nα-benzyloxycarbonyl-Nβ-tert-butyloxycarbonyl-D-2,3-diaminopropionic acid (159002-15-0,62234-36-0) → (R)-2-benzyloxycarbonylamino-3-tert-butoxycarbonylamino-N-methoxy-N-methylpropanamide (173259-64-8)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; dicyclohexyl-carbodiimide; Yield given. Multistep reaction; 1.) CH₂Cl₂, 0 deg C, 4.5 h; 2.) CH₂Cl₂, 2 h, 0 deg C then 20 h, r.t.;

DOI:10.1055/s-1995-4111

upstream raw materials:

N,O-dimethylhydroxylamine*hydrochloride

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

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

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