Methanesulfonyl chloride → HCID 42639485, 화합물

HRID 1351397노트

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HRID 1351397 반응식
[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]

참가 물질

5

반응물 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

생성물 1

HCID 42639485HCID 42639485, 화합물

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

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온도
-5 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d70d77f6910148c3a09b2e8be070323f
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07217731B2

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