tert-butyl 2-((2S,5R)-6-(benzyloxy)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-4-yl)ethylcarbamate → tert-butyl 2-((2S,5R)-2-carbamoyl-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-4-yl)ethylcarbamate

HRID 627240Notes

Reaction equation

HRID 627240 reaction equation
C([O:8][N:9]1[C:15](=[O:16])[N:14]2[CH2:17][C@H:10]1[C:11]([CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:12][C@H:13]2[C:18](=[O:20])[NH2:19])C1C=CC=CC=1>CCOC(C)=O.[Pd]>[C:18]([C@@H:13]1[CH:12]=[C:11]([CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[C@@H:10]2[CH2:17][N:14]1[C:15](=[O:16])[N:9]2[OH:8])(=[O:20])[NH2:19]

Participants

4

Reactant 1

HCID 89852204tert-butyl 2-((2S,5R)-6-(benzyloxy)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-4-yl)ethylcarbamate2×

Product 1

HCID 117940260tert-butyl 2-((2S,5R)-2-carbamoyl-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-4-yl)ethylcarbamateYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 2-((2S,5R)-6-(benzyloxy)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-4-yl)ethylcarbamate (Intermediate 227, 0.300 g, 0.72 mmol) in EtOAc (5 mL) was added 10% Pd/C (0.077 g, 0.72 mmol). The reaction mixture was stirred under hydrogen for 30 minutes. The reaction mixture was filtered through celite and washed with EtOAc. The solvent was removed in vacuo to give the title compound as a white solid (0.23 g, 98%).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed with EtOAc
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-3226fa1876a445bbbe3ad8e1a9561a21
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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