HCID 86694033, compound → HCID 86694034, compound

HRID 2400703Notes

Reaction equation

HRID 2400703 reaction equation
C([O:8][N:9]1[C:15](=[O:16])[N:14]2[CH2:17][C@H:10]1[CH2:11][CH2:12][C@@H:13]2[C:18]([NH:20][NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[O:19])C1C=CC=CC=1.[H][H]>CO.[Pd]>[OH:8][N:9]1[C:15](=[O:16])[N:14]2[CH2:17][C@H:10]1[CH2:11][CH2:12][C@@H:13]2[C:18]([NH:20][NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[O:19]

Participants

5

Reactant 2

HCID 86694033HCID 86694033, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86694034HCID 86694034, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (2R,5R)-6-(benzyloxy)-N′-(methylsulfonyl)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide 188 (0.37 g, 1.044 mml) in methanol (35 mL) was added 5% Pd/C (0.40 g). The mixture was hydrogenated under 10 psi hydrogen atmosphere at room temperature for 1 h. The catalyst was filtered through Celite and the filtrate was evaporated to give (2R,5R)-6-hydroxy-N′-(methylsulfonyl)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide 189 (0.276 g, 99%) as a colorless foam.

Workup

  1. filtrationThe catalyst was filtered through Celite
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-f343afa05a1f43ef8adab3337d3e864c
Source dataset
uspto-grants-2014_08
Patent number
US08796257B2

Reaction notes

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