Water → HCID 86705179, compound

HRID 2401278Notes

Reaction equation

HRID 2401278 reaction equation
[H-].[Na+].C([O:10][C:11](=O)[NH:12][C@@H:13]([C@@H:27]([F:30])[CH2:28][CH3:29])[CH2:14][NH:15][C:16]1[C:21]([F:22])=[CH:20][C:19]([C:23]([F:26])([F:25])[F:24])=[CH:18][N:17]=1)C1C=CC=CC=1.O>C1COCC1>[F:30][C@H:27]([C@H:13]1[CH2:14][N:15]([C:16]2[C:21]([F:22])=[CH:20][C:19]([C:23]([F:26])([F:25])[F:24])=[CH:18][N:17]=2)[C:11](=[O:10])[NH:12]1)[CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 131731732HCID 131731732, compound

Product 1

HCID 86705179HCID 86705179, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (about 60%, 546 mg) was added to a solution of benzyl[(2R,3S)-3-fluoro-1-{[3-fluoro-5-(trifluoromethyl)pyridin-2-yl]amino}pentan-2-yl]carbamate (2.85 g) in THF (35 mL), and the mixture was stirred at room temperature for 6 hr. Water was added to the reaction mixture, the resulting mixture was extracted with ethyl acetate, and the organic layer was washed with brine. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate=80:20-40:60) to afford the title compound (2.07 g).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with brine
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate=80:20-40:60)

Sources & evidence

ORD record
ord-c53afc3918f94afbbaa126093a780933
Source dataset
uspto-grants-2014_08
Patent number
US08796272B2

Reaction notes

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