(2S,5R)-tert-butyl 6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylate

Base Information

• Chemical Name: (2S,5R)-tert-butyl 6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylate
• CAS No.: 1383814-56-9
• Molecular Formula: C₁₈H₂₄N₂O₄
• Molecular Weight: 332.4
• Mol file: 1383814-56-9.mol

Synonyms:(2S,5R)-tert-butyl 6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylate

Chemical Property of (2S,5R)-tert-butyl 6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5R)-tert-butyl 6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylate

There total 14 articles about (2S,5R)-tert-butyl 6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylate 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: 69.0%

(2S,5R)-tert-butyl 5-(benzyloxyamino)piperidine-2-carboxylate (1383814-55-8) + trichloromethyl chloroformate (503-38-8) → (2S,5R)-tert-butyl 6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylate (1383814-56-9)

Guidance literature:

(2S,5R)-tert-butyl 5-(benzyloxyamino)piperidine-2-carboxylate; trichloromethyl chloroformate; With triethylamine; In acetonitrile; at 0 ℃; for 0.25h; Inert atmosphere;

With dmap; In acetonitrile; at 0 - 20 ℃; for 3h;

Reference yield: 69.0%

phosgene (75-44-5) + (2S,5R)-tert-butyl 5-(benzyloxyamino)piperidine-2-carboxylate (1383814-55-8) → (2S,5R)-tert-butyl 6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylate (1383814-56-9)

Guidance literature:

With dmap; triethylamine; In acetonitrile; at 20 ℃; Inert atmosphere;

Reference yield: 66.0%

(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid (1174020-25-7,2064219-13-0) + tert-butyl alcohol (75-65-0) → (2S,5R)-tert-butyl 6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylate (1383814-56-9)

Guidance literature:

With pyridine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.1c00799

upstream raw materials:

(2S,5R)-tert-butyl 5-(benzyloxyamino)piperidine-2-carboxylate

trichloromethyl chloroformate

tert-butyl N-benzyloxycarbonyl-L-pyroglutamate

(2S)-5-oxopiperidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

Downstream raw materials:

(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid cyclohexylamine salt

(1R,2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

(2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid