tert-Butyl (4S)-4-({[(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)azepane-1-carboxylate → tert-Butyl (4S)-4-({[(2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)azepane-1-carboxylate

HRID 451302Notes

Reaction equation

HRID 451302 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][C@H:21]1[CH2:27][CH2:26][CH2:25][N:24]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:23][CH2:22]1)=[O:19])C1C=CC=CC=1>[Pd].CO>[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][C@H:21]1[CH2:27][CH2:26][CH2:25][N:24]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:23][CH2:22]1)=[O:19]

Participants

4

Reactant 1

HCID 86659585tert-Butyl (4S)-4-({[(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)azepane-1-carboxylate

Product 1

HCID 86659586tert-Butyl (4S)-4-({[(2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)azepane-1-carboxylateYield 35.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium on carbon (11.8 mg; 10% Pd/C) was added to a solution of tert-butyl (4S)-4-({[(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)azepane-1-carboxylate (49.7 mg, 0.33 mmol) in methanol (1.5 mL) and the resulting mixture was stirred under hydrogen (balloon) for 3 hours. TLC analysis showed the reaction was complete. The reaction mixture was filtered through a microfilter and the filtrate was concentrated under vacuum to afford the impure title compound as a white foam (44.8 mg) which was used without purification in the next step.

Workup

  1. filtrationThe reaction mixture was filtered through a microfilter
  2. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-3ff4fb84f79946acb5d90fd129fe6fb3
Source dataset
uspto-grants-2013_07
Patent number
US08487093B2

Reaction notes

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