Water → HCID 19434882, compound

HRID 1736155Notes

Reaction equation

HRID 1736155 reaction equation
[N:1]([C:4]1[C:14]([F:15])=[C:13]([NH:16][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([O:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[C:5]=1[F:30])=[N+]=[N-].[BH4-].[Na+].O>CO>[NH2:1][C:4]1[C:14]([F:15])=[C:13]([NH:16][C:17](=[O:22])[C:18]([CH3:20])([CH3:21])[CH3:19])[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([O:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[C:5]=1[F:30]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 19434959HCID 19434959, compound

Product 1

HCID 19434882HCID 19434882, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4.64 g (10.9 mmol) of the above ethyl 4-azido-3,5-difluoro-6-pivaloylamino-2-(2-tetrahydropyranyloxy)benzoate was dissolved in 100 mL of methanol, 2.90 g (76.7 mmol) of sodium borohydride was added in several portions under ice-cooling, 10 mL of water was further added and the mixture was stirred at room temperature for 4.5 hours. The solvent was distilled off under reduced pressure, water was added and the mixture was extracted once with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol=100:1) to give 4.09 g of ethyl 4-amino-3,5-difluoro-6-pivaloylamino-2-(2-tetrahydropyranyloxy)benzoate (yield: 94%).

Workup

  1. temperaturecooling
  2. distillationThe solvent was distilled off under reduced pressure, water
  3. additionwas added
  4. extractionthe mixture was extracted once with ethyl acetate
  5. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (chloroform:methanol=100:1)

Sources & evidence

ORD record
ord-240ccb0ad0074052a97bffc6291f96b9
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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