Ammonium formate → HCID 89893894, compound

HRID 925431Notes

Reaction equation

HRID 925431 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][N:8]1[CH2:12][C@H:11]([CH2:13][O:14]CC2C=CC=CC=2)[O:10][C:9]1=[O:22])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>C(O)C.[Pd]>[OH:14][CH2:13][C@@H:11]1[O:10][C:9](=[O:22])[N:8]([NH:7][C:6](=[O:23])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:12]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 89894078HCID 89894078, compound

Product 1

HCID 89893894HCID 89893894, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a suspension of (R)-tert-butyl-5-(benzyloxymethyl)-2-oxooxazolidin-3-ylcarbamate (1.908 g, 5.92 mmol) and 10% Pd/C (315 mg, 0.296 mmol) in ethanol (25 mL), ammonium formate (933 mg, 14.80 mmol) was added and the reaction was refluxed, under nitrogen, while stirring for 3 h 30 min. The catalyst was filtered away and the solvent evaporated. The residue was triturated with diisopropyl ether:MeOH=10:1. The title compound was obtained as a white solid (852 mg, 3.67 mmol). Yield=62%.

Workup

  1. additionwas added
  2. temperaturethe reaction was refluxed, under nitrogen
  3. filtrationThe catalyst was filtered away
  4. customthe solvent evaporated
  5. customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-456a2a1b6654427ea1ec70060c53657a
Source dataset
uspto-grants-2016_03
Patent number
US09284306B2

Reaction notes

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