Reaction #1135860

ord-a6bfc701fe614ace8088df0eac8f7ea2

Reaction equation

CC(C)(C)OC(=O)N1CC[C@@H](C(=O)NNC(=O)[C@H]2CC[C@@H]3CN2C(=O)N3OCc2ccccc2)C1
trans-3-[N′-(6-benzyloxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)-hydrazinocarbonyl]-(R)-pyrrolidin-1-carboxylic acid tert-butyl ester
→
CC(C)(C)OC(=O)N1CC[C@@H](C(=O)NNC(=O)[C@H]2CC[C@@H]3CN2C(=O)N3O)C1
title compound
CC(C)(C)OC(=O)N1CC[C@@H](C(=O)NNC(=O)[C@H]2CC[C@@H]3CN2C(=O)N3O)C1
trans-3-[N′-(6-hydroxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)-hydrazinocarbonyl]-(R)-pyrrolidin-1-carboxylic acid tert-butyl ester

Reactants

CC(C)(C)OC(=O)N1CC[C@@H](C(=O)NNC(=O)[C@H]2CC[C@@H]3CN2C(=O)N3OCc2ccccc2)C1
trans-3-[N′-(6-benzyloxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)-hydrazinocarbonyl]-(R)-pyrrolidin-1-carboxylic acid tert-butyl ester

Reagents

[Pd]
palladium on carbon

Solvents

CO
methanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

By using the procedure described in Step-2 of Example-1, and by using trans-3-[N′-(6-benzyloxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)-hydrazinocarbonyl]-(R)-pyrrolidin-1-carboxylic acid tert-butyl ester (11.5 gm, 0.024 mol), methanol (115 ml) and 10% palladium on carbon (3.0 gm) to provide the title compound in 9.5 gm quantity as a pale brown solid and it was used for the next reaction immediately.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09381200B2uspto-grants-2016_07