HCID 86699617, compound → HCID 86699616, compound

HRID 2400749Notes

Reaction equation

HRID 2400749 reaction equation
[C:1]([O:5][C:6](=[O:43])[NH:7][C:8]([N:17]1[CH2:21][CH2:20][C@H:19]([O:22][NH:23][C:24]([C@@H:26]2[CH2:32][CH2:31][C@@H:30]3[CH2:33][N:27]2[C:28](=[O:42])[N:29]3[O:34]CC2C=CC=CC=2)=[O:25])[CH2:18]1)=[N:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:12]([O:11][C:10](=[O:16])[NH:9][C:8]([N:17]1[CH2:21][CH2:20][C@H:19]([O:22][NH:23][C:24]([C@@H:26]2[CH2:32][CH2:31][C@@H:30]3[CH2:33][N:27]2[C:28](=[O:42])[N:29]3[OH:34])=[O:25])[CH2:18]1)=[N:7][C:6](=[O:43])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:13])([CH3:14])[CH3:15]

Participants

4

Reactant 1

HCID 86699617HCID 86699617, compound

Product 1

HCID 86699616HCID 86699616, compoundYield 97.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of di-tert-butyl[{(3S)-3-[({[(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]pyrrolidin-1-yl}methylylidene]biscarbamate 279 (0.34 g, 0.56 mmol) and Pd/C (0.15 g) in methanol (20 mL) was hydrogenated at 1 atm at room temperature for 3 h. The mixture was filtered through Celite pad and concentrated to provide 280 (0.28 g, 97%) as white solid.

Workup

  1. filtrationThe mixture was filtered through Celite pad
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-4a4176abe834478eae3a739af1f22c60
Source dataset
uspto-grants-2014_08
Patent number
US08796257B2

Reaction notes

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