Hydrochloric Acid → HCID 10814962, compound

HRID 1489426Notes

Reaction equation

HRID 1489426 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]([CH:33]=[O:34])([OH:32])[C@H:10]([N:12]1[C:16](=[O:17])[N:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]([F:31])([F:30])[CH:27]([F:29])[F:28])=[CH:20][CH:19]=2)[CH:14]=[N:13]1)[CH3:11].[BH4-].[Na+].Cl.C(OCC)(=O)C>CO>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]([OH:32])([CH2:33][OH:34])[C@H:10]([N:12]1[C:16](=[O:17])[N:15]([C:18]2[CH:19]=[CH:20][C:21]([O:24][CH2:25][C:26]([F:31])([F:30])[CH:27]([F:29])[F:28])=[CH:22][CH:23]=2)[CH:14]=[N:13]1)[CH3:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 10791195HCID 10791195, compound

Product 1

HCID 10814962HCID 10814962, compoundYield 54.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-[(1R,2S)-2-(2,4-Difluorophenyl)-2-formyl-2-hydroxy-1-methylethyl]-4-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-3(2H,4H)-1,2,4-triazolone (300 mg) was dissolved in 9 ml of methanol, to which 74 mg of sodium borohydride was added at 0° C. The mixture was stirred with ice cooling for 30 minutes. To the reaction solution was added 1 ml of 1N-hydrochloric acid and 50 ml of ethyl acetate, and then the organic layer was washed with 10 ml of water and 10 ml of an aqueous solution of sodium chloride successively. The organic layer was dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent; hexane:ethyl acetate=1:1) to give 165 mg of 2-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-dihydroxy-1-methylpropyl]-4-[4-(2,2,3,3-tetrafluoro-propoxy)phenyl]-3(2H,4H)-1,2,4-triazolone as colorless prisms.

Workup

  1. additionwas added at 0° C
  2. washthe organic layer was washed with 10 ml of water and 10 ml of an aqueous solution of sodium chloride successively
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel chromatography (eluent; hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-baa64133636e47bbaf53f993d2a061d8
Source dataset
uspto-grants-1997_10
Patent number
US05677464

Reaction notes

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