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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 627258Generated: October 30, 2026

4-(2-Acetamidoethyl)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamide → (2S,5R)-4-(2-acetamidoethyl)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamide

https://huagongshe.com/reaction/627258

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-(2-Acetamidoethyl)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamideHCID 89852500—
Reactant(2S,5R)-4-(2-acetamidoethyl)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamideHCID 89863102—
CatalystPalladiumHCID 23938—
SolventEthanolHCID 702—
SolventEthyl AcetateHCID 8857—
Product(2S,5R)-4-(2-acetamidoethyl)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamideHCID 89852077101.7%

Reaction Steps

To a solution of 4-(2-acetamidoethyl)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamide (Intermediate 247, 0.120 g, 0.33 mmol) in EtOAc (20 mL) and ethanol (6.67 mL) was added Pd/C (0.036 g, 0.33 mmol). The reaction mixture was stirred under hydrogen at 1 atm for 1 hour, then filtered through celite and concentrated to dryness to afford the title compound as a white solid (0.09 g, 100%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09309245B2
Source datasetuspto-grants-2016_04
ORD IDord-7b2b6ba395cc4a35818b90a1cabd906f
Source noteuspto-grants-2016_04