Methanesulfonyl chloride → HCID 42639485, compound

HRID 1351397Notes

Reaction equation

HRID 1351397 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:4]=[C:5]([C@H:13]([O:15][C@H:16]2[CH2:21][CH2:20][C@H:19]([CH2:22][OH:23])[C@@H:18]([CH2:24][OH:25])[C@@H:17]2[C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:35][S:36]([O:23][CH2:22][C@H:19]1[CH2:20][CH2:21][C@H:16]([O:15][C@@H:13]([C:5]2[CH:4]=[C:3]([C:2]([F:1])([F:33])[F:34])[CH:8]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:6]=2)[CH3:14])[C@@H:17]([C:26]2[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=2)[C@@H:18]1[CH2:24][O:25][S:36]([CH3:35])(=[O:38])=[O:37])(=[O:38])=[O:37]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 42639484((1S,2R,3R,4S)-4-((R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy)-3-(4-fluorophenyl)cyclohexane-1,2-diyl)dimethanol

Product 1

HCID 42639485HCID 42639485, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

To a solution of 1.82 g (3.7 mmol) [(1S,2R,3R,4S)-4-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-3-(4-fluorophenyl)cyclohexane-1,2-diyl]dimethanol (step G) in 50 mL methylene chloride cooled to −5° C. in an ice/salt bath was added 1.0 mL (3.5 equiv.) methane-sulfonyl chloride; 2.1 mL (4 equiv.) TEA and 44 mg (0.1 equiv.) DMAP. The reaction mixture was stirred at −5° C. for 30 min then quenched at that temperature by the addition of 20 mL sat. aq. NaHCO3. The mixture was warmed to RT. The organic layer was separated and the aqueous layer extracted with additional 50 mL methylene chloride. The combined organic layer was washed with 20 mL 2N aq. HCl, 30 mL sat. aq. NaHCO3, brine, dried over MgSO4 drying agent, filtered and the solvent evaporated under vacuum to give the title compound as an oil which was used without further purification.

Workup

  1. customthen quenched at that temperature by the addition of 20 mL sat. aq. NaHCO3
  2. temperatureThe mixture was warmed to RT
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted with additional 50 mL methylene chloride
  5. washThe combined organic layer was washed with 20 mL 2N aq. HCl, 30 mL sat. aq. NaHCO3, brine
  6. dry with materialdried over MgSO4 drying agent
  7. filtrationfiltered
  8. customthe solvent evaporated under vacuum

Sources & evidence

ORD record
ord-d70d77f6910148c3a09b2e8be070323f
Source dataset
uspto-grants-2007_05
Patent number
US07217731B2

Reaction notes

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