Potassium Carbonate → HCID 15234271, compound

HRID 2395689Notes

Reaction equation

HRID 2395689 reaction equation
Br[CH:2]([CH3:5])[C:3]#[N:4].C(=O)([O-])[O-].[K+].[K+].[F:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[C@:20]([OH:30])([C@H:27]([SH:29])[CH3:28])[CH2:21][N:22]1[CH:26]=[N:25][CH:24]=[N:23]1>CN(C)C=O.C1C=CC=CC=1>[C:3]([CH:2]([S:29][C@H:27]([CH3:28])[C@:20]([C:14]1[CH:15]=[CH:16][C:17]([F:19])=[CH:18][C:13]=1[F:12])([OH:30])[CH2:21][N:22]1[CH:26]=[N:25][CH:24]=[N:23]1)[CH3:5])#[N:4]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1405382-BromopropionitrileHCID 1922642-(2,4-Difluorophenyl)-3-mercapto-1-(1H-1,2,4-triazol-1-yl)-2-butanol

Product 1

HCID 15234271HCID 15234271, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6228DimethylformamideSolvent

Procedure

134 mg (1.00 mmole) of 2-bromopropionitrile and 69 mg (0.50 mmole) of potassium carbonate were added to a solution of 143 mg (0.50 mmole) of (2R,3R)-2-(2,4-difluorophenyl)-3-mercapto-1-(1H-1,2,4-triazol-1-yl)-2-butanol in 3 ml of dimethylformamide, and the resulting mixture was stirred at room temperature for 1 hour under an atmosphere of nitrogen. The reaction mixture was then dissolved in benzene, and the resulting solution was washed, in turn, with water and with a saturated aqueous solution of sodium chloride. The solvent was then removed by distillation under reduced pressure, after which the resulting oily residue was purified by preparative thin layer chromatography on silica gel, using a 3:2 by volume mixture of ethyl acetate and hexane as the developing solvent, to afford 57 mg of stereoisomer A of the title compound (having the lower polarity) as an oil and 72 mg of stereoisomer B of the title compound (having the higher polarity) as crystals; these crystals were recrystallized from a mixture of benzene and hexane to give a pure specimen melting at 66°-68° C.

Workup

  1. washthe resulting solution was washed, in turn, with water and with a saturated aqueous solution of sodium chloride
  2. customThe solvent was then removed by distillation under reduced pressure
  3. customafter which the resulting oily residue was purified by preparative thin layer chromatography on silica gel
  4. additionby volume mixture of ethyl acetate and hexane as the developing solvent

Sources & evidence

ORD record
ord-5e2a44cfaf384ea9abeb87512921d430
Source dataset
uspto-grants-1996_02
Patent number
US05489606

Reaction notes

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