Water → HCID 21700819, compound

HRID 1870792Notes

Reaction equation

HRID 1870792 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH:19]3[CH2:24][C:23](=[O:25])[C:22]4[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=4[S:20]3(=[O:31])=[O:30])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1.O>CO>[F:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][CH2:18][CH:19]3[CH2:24][CH:23]([OH:25])[C:22]4[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=4[S:20]3(=[O:30])=[O:31])[CH2:14][CH2:15]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 15871419HCID 15871419, compound

Product 1

HCID 21700819HCID 21700819, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

340 mg (9 mmol) of sodium borohydride was added to a suspension of 375 mg (0.9 mmol) of the Compound 19 in 15 ml of methanol while stirring under cooling with ice. After stirring for two hours at room temperature, 15 ml of water was added and the mixture was stirred for one hour at room temperature and concentrated under vacuum. Ethyl acetate was added to the residue and the organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. The crude product was purified by recrystallizing from ethanol to obtain 230 mg (yield: 61%) of the title compound.

Workup

  1. temperatureunder cooling with ice
  2. stirringAfter stirring for two hours at room temperature
  3. stirringthe mixture was stirred for one hour at room temperature
  4. concentrationconcentrated under vacuum
  5. additionEthyl acetate was added to the residue
  6. washthe organic layer was washed with water and saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under vacuum
  9. customThe crude product was purified
  10. customby recrystallizing from ethanol

Sources & evidence

ORD record
ord-378871a5e509463d919c691f5dc5e22d
Source dataset
uspto-grants-2000_08
Patent number
US06100265

Reaction notes

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