Triethylamine → HCID 59367763, 화합물

HRID 1643458

반응식

HRID 1643458 반응식
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([S:12]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]2[CH2:21][OH:22])(=[O:14])=[O:13])=[C:7]([CH3:23])[CH:6]=1.C(N(CC)CC)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>CCCCCC.CN(C)C=O.O>[CH3:31][S:32]([O:22][CH2:21][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][N:15]1[S:12]([C:8]1[C:7]([CH3:23])=[CH:6][C:5]([O:4][CH3:3])=[CH:10][C:9]=1[CH3:11])(=[O:13])=[O:14])(=[O:34])=[O:33]

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 43574491[1-(4-Methoxy-2,6-dimethyl-phenylsulfonyl)-piperidin-2-yl]-methanol

생성물 1

HCID 59367763HCID 59367763, 화합물

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매2회HCID 8058Hexane용매

실험 절차

Sodium hydride (0.346 g, 8.679 mmol, 60%), washed with hexane and dried with an inert gas, was initially introduced into N,N-dimethylformamide (10 ml) under an inert gas, (1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)methanol (1.36 g, 4.34 mmol) was added and the mixture was then stirred at room temperature for 30 min. Triethylamine (1.8 ml, 13.019 mmol) was added, the reaction mixture was cooled with ice-water, and methanesulfonyl chloride (0.838 ml, 10.849 mmol) in N,N-dimethylformamide (10 ml) was slowly added dropwise. After stirring at room temperature for 1 h, 5 ml of water were added and the solvent was removed in vacuo. The residue was taken up in saturated sodium bicarbonate solution (20 ml) and ethyl acetate (50 ml), the phases were separated and the aqueous phase was extracted with ethyl acetate (2×50 ml). The combined organic phases were washed with saturated sodium chloride solution (40 ml), dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (silica gel) with diethyl ether/hexane/methylene chloride (1:1:1). Yield: 1.66 g (97%)

후처리

  1. customdried with an inert gas
  2. additionwas added
  3. additionwas slowly added dropwise
  4. stirringAfter stirring at room temperature for 1 h
  5. customthe solvent was removed in vacuo
  6. customethyl acetate (50 ml), the phases were separated
  7. extractionthe aqueous phase was extracted with ethyl acetate (2×50 ml)
  8. washThe combined organic phases were washed with saturated sodium chloride solution (40 ml)
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated in vacuo
  11. customThe crude product was purified by column chromatography (silica gel) with diethyl ether/hexane/methylene chloride (1:1:1)

출처 및 근거

ORD 기록
ord-3997df5073844e4c8da2b08bce70fb71
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08119805B2

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