HCID 86699601, compound → HCID 86699602, compound

HRID 2400647Notes

Reaction equation

HRID 2400647 reaction equation
[C:1]([O:5][C:6](=[O:35])[NH:7][S:8](=[O:34])(=[O:33])[NH:9][CH2:10][CH2:11][O:12][NH:13][C:14]([C@@H:16]1[CH2:22][CH2:21][C@@H:20]2[CH2:23][N:17]1[C:18](=[O:32])[N:19]2[O:24]CC1C=CC=CC=1)=[O:15])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:35])[NH:7][S:8](=[O:33])(=[O:34])[NH:9][CH2:10][CH2:11][O:12][NH:13][C:14]([C@@H:16]1[CH2:22][CH2:21][C@@H:20]2[CH2:23][N:17]1[C:18](=[O:32])[N:19]2[OH:24])=[O:15])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 86699601HCID 86699601, compound

Product 1

HCID 86699602HCID 86699602, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of tert-butyl({2-[({[(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]ethyl}sulfamoyl)carbamate 79 (0.35 g, 0.67 mmol) and Pd/C (10%, 0.12 g) in methanol (10 mL) was hydrogenated at 1 atm at room temperature for 3 h. The mixture was filtered through Celite pad and concentrated to provide 80 (0.25 g, 88%) as a white foam.

Workup

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

Sources & evidence

ORD record
ord-0a98ba1e9d824590ac3571d51e382807
Source dataset
uspto-grants-2014_08
Patent number
US08796257B2

Reaction notes

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