Methanesulfonyl chloride → HCID 10674539, compound

HRID 1489433Notes

Reaction equation

HRID 1489433 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]([OH:34])([CH2:32][OH:33])[C@H:10]([N:12]1[CH:16]=[CH:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]([F:30])([F:29])[CH:26]([F:28])[F:27])=[CH:19][CH:18]=2)[C:13]1=[O:31])[CH3:11].[CH3:35][S:36](Cl)(=[O:38])=[O:37]>C(OCC)(=O)C.C(N(CC)CC)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]([OH:34])([CH2:32][O:33][S:36]([CH3:35])(=[O:38])=[O:37])[C@H:10]([N:12]1[CH:16]=[CH:15][N:14]([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH2:24][C:25]([F:30])([F:29])[CH:26]([F:28])[F:27])=[CH:21][CH:22]=2)[C:13]1=[O:31])[CH3:11]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 11799245HCID 11799245, compound

Product 1

HCID 10674539HCID 10674539, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

1-[(1R,2S)-2-(2,4-Difluorophenyl)-2,3-dihydroxy-1-methylpropyl]-3-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-2(1H,3H)-imidazolone (1.2 g) was dissolved in 25 ml of ethyl acetate, to which 0.29 ml of methanesulfonyl chloride and 0.53 ml of triethylamine were added dropwise with ice cooling. After stirring at 0° C. for 30 minutes, the reaction solution was washed with water (15 ml×2) and 15 ml of an aqueous solution of sodium chloride successively. The organic layer was dried over magnesium sulfate. After the solvent was distilled off under reduced pressure, the residue was purified by silica gel chromatography (silica gel: 50 g, eluent; hexane:ethyl acetate=1:1). The desired fraction was concentrated and the residue was recrystallized from a mixture of 5 ml of diisopropyl ether and 10 ml of hexane to give 1.26 g of 1-[(1R,2S)-2-(2,4-difluorophenyl)-2-hydroxy-3-methanesulfonyloxy-1-methylpropyl]-3-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-2(1H,3H)-imidazolone as colorless powdery crystals.

Workup

  1. additionwere added dropwise with ice cooling
  2. washthe reaction solution was washed with water (15 ml×2) and 15 ml of an aqueous solution of sodium chloride successively
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. distillationAfter the solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel chromatography (silica gel: 50 g, eluent; hexane:ethyl acetate=1:1)
  6. concentrationThe desired fraction was concentrated
  7. customthe residue was recrystallized from a mixture of 5 ml of diisopropyl ether and 10 ml of hexane

Sources & evidence

ORD record
ord-651416d56e064a01b018fa1e2e12341d
Source dataset
uspto-grants-1997_10
Patent number
US05677464

Reaction notes

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