Methanesulfonyl chloride → HCID 10674287, compound

HRID 1489437Notes

Reaction equation

HRID 1489437 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]([OH:33])([CH2:31][OH:32])[C@H:10]([N:12]1[CH:16]=[CH:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]([F:29])([F:28])[CH:25]([F:27])[F:26])=[CH:19][CH:18]=2)[C:13]1=[O:30])[CH3:11].[CH3:34][S:35](Cl)(=[O:37])=[O:36]>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:33])([CH2:31][O:32][S:35]([CH3:34])(=[O:37])=[O:36])[C@H:10]([N:12]1[CH:16]=[CH:15][N:14]([C:17]2[CH:18]=[CH:19][C:20]([O:23][C:24]([F:29])([F:28])[CH:25]([F:27])[F:26])=[CH:21][CH:22]=2)[C:13]1=[O:30])[CH3:11]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 10695920HCID 10695920, compound

Product 1

HCID 10674287HCID 10674287, 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-(1,1,2,2-tetrafluoroethoxy)phenyl]-2(1H,3H)-imidazolone (0.5 g) was dissolved in 20 ml of ethyl acetate, to which 0.12 ml of methanesulfonyl chloride and 0.22 ml of triethylamine were added dropwise with ice cooling. After stirring at 0° C. for 30 minutes, the reaction solution was washed with water (10 ml×2) and 10 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 to give 0.58 g of 1-[(1R,2S)-2-(2,4-difluorophenyl)-2-hydroxy-3-methanesulfonyloxy-1-methylpropyl]-3-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-2(1H,3H)-imidazolone as a colorless oil.

Workup

  1. additionwere added dropwise with ice cooling
  2. washthe reaction solution was washed with water (10 ml×2) and 10 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

Sources & evidence

ORD record
ord-28586770341f4e1294b2333c5e40263f
Source dataset
uspto-grants-1997_10
Patent number
US05677464

Reaction notes

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