HCID 68760397, compound → 1,1-Dimethylethyl 4-[[[(1R,2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl]amino]-1-piperidinecarboxylate

HRID 451297Notes

Reaction equation

HRID 451297 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][CH:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]1)=[O:19])C1C=CC=CC=1>[Pd].CO.C(O)(=O)C>[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][CH:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]1)=[O:19]

Participants

5

Reactant 1

HCID 68760397HCID 68760397, compound

Product 1

HCID 452589641,1-Dimethylethyl 4-[[[(1R,2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl]amino]-1-piperidinecarboxylate

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 23938PalladiumCatalyst3×HCID 887MethanolSolvent

Procedure

Palladium on carbon (394 mg; 10% Pd/C) was added to a solution of the product of step 1 (1.81 g, 3.95 mmol) in methanol (50.6 mL) and the resulting mixture was stirred under hydrogen (balloon) overnight. LC/MS analysis indicated the reaction was not complete. Acetic acid (6 drops) and additional catalyst (159 mg of 10% Pd/C) were added to the reaction and the resulting mixture was stirred under hydrogen (balloon) for an additional 90 minutes. Additional catalyst (0.2085 g of 10% Pd/C) was added to the reaction and stirring under hydrogen was continued for an additional 2.5 hours at which time the reaction was judged complete by LC-MS analysis. The reaction was filtered through a celite pad and the collected solid was washed well with MeOH. The filtrate was concentrated under vacuum to afford the title compound as a colorless oil which was used without purification in the next step.

Workup

  1. stirringthe resulting mixture was stirred under hydrogen (balloon) for an additional 90 minutes
  2. stirringstirring under hydrogen
  3. waitwas continued for an additional 2.5 hours at which time
  4. filtrationThe reaction was filtered through a celite pad
  5. washthe collected solid was washed well with MeOH
  6. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-3bb8cf48b28143cd894fcb6812c3e7df
Source dataset
uspto-grants-2013_07
Patent number
US08487093B2

Reaction notes

Loading…