Water → (2S,3R)-2-(2,4-Difluorophenyl)-3-(pyrimidin-4-yl)butan-1,2-diol

HRID 1196955Notes

Reaction equation

HRID 1196955 reaction equation
[OH-].[Na+].C([O:6][CH2:7][C@:8]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[F:25])([OH:17])[C@@H:9]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][N:12]=1)[CH3:10])(=O)C.O>CO>[F:25][C:19]1[CH:20]=[C:21]([F:24])[CH:22]=[CH:23][C:18]=1[C@@:8]([OH:17])([C@@H:9]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][N:12]=1)[CH3:10])[CH2:7][OH:6]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 57184320(2S,3R)-1-Acetoxy-2-(2,4-difluorophenyl)-3-(pyrimidin-4-yl)butan-2-ol

Product 1

HCID 57290484(2S,3R)-2-(2,4-Difluorophenyl)-3-(pyrimidin-4-yl)butan-1,2-diolYield 85.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2N Sodium hydroxide solution (40 ml) was added with stirring over 0.25 hour to a solution of the product of part (ii) (23.3 g) in methanol (80 ml) and stirring was continued for a further 0.25 hour. Water (150 ml) was added and the mixture was cooled. The solid was filtered off, washed with water and dried to give the title compounds, (17.4 g), m.p. 148.5°-150.5°.

Workup

  1. temperaturethe mixture was cooled
  2. filtrationThe solid was filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-308271e247224babbef4950174a62fd1
Source dataset
uspto-grants-1992_05
Patent number
US05116844

Reaction notes

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