4-Toluenesulfonyl chloride → [2-Methyl-7,8-dihydro[1,4]dioxino[2,3-g][1,3]benzoxazol-8-yl]methyl 4-methylbenzenesulfonate

HRID 1072443

반응식

HRID 1072443 반응식
[CH3:1][C:2]1[O:3][C:4]2[C:10]3[O:11][C@@H:12]([CH2:15][OH:16])[CH2:13][O:14][C:9]=3[CH:8]=[CH:7][C:5]=2[N:6]=1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:27][C:17]1[CH:22]=[CH:21][C:20]([S:23]([O:16][CH2:15][CH:12]2[CH2:13][O:14][C:9]3[CH:8]=[CH:7][C:5]4[N:6]=[C:2]([CH3:1])[O:3][C:4]=4[C:10]=3[O:11]2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

참가 물질

6

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 69017866HCID 69017866, 화합물

생성물 1

HCID 11268854[2-Methyl-7,8-dihydro[1,4]dioxino[2,3-g][1,3]benzoxazol-8-yl]methyl 4-methylbenzenesulfonate

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매3회

실험 절차

To a solution of [(8S)-2-methyl-7,8-dihydro[1,4]dioxino[2,3-g)[1,3]benzoxazol-8-yl]methanol (1.80 g, 8.14 mmole) in methylene chloride (100 mL) was added p-toluenesulfonyl chloride (3.90 g, 20.4 mmole). The mixture was cooled in an ice bath and a solution of diisopropylethylamine (3.55 mL, 20.4 mmole) in methylene chloride (20 mL) was then added dropwise, followed by 4-dimethylaminopyridine (0.65 g, 5.30 mmole). The solution was allowed to warm to room temperature and was stirred under nitrogen overnight. The reaction was diluted to 500 mL in volume with methylene chloride, then washed with aqueous 2 N HCl (200 mL), with saturated aqueous sodium bicarbonate (200 mL), and with brine (150 mL), dried over magnesium sulfate, filtered and evaporated in vacuum to a yellow oil. The crude oil was column chromatographed on silica gel using methylene chloride to remove impurities and 3% methanol/methylene chloride to elute the (R)-enantiomer of the title compound, which becomes a white solid under vacuum (2.56 g, 84%), m.p. 123° C. MS (ESI) m/z 376 (M+H)+.

후처리

  1. temperatureThe mixture was cooled in an ice bath
  2. washwashed with aqueous 2 N HCl (200 mL), with saturated aqueous sodium bicarbonate (200 mL)
  3. dry with materialwith brine (150 mL), dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuum to a yellow oil
  6. customchromatographed on silica gel
  7. customto remove impurities and 3% methanol/methylene chloride
  8. washto elute the (R)-enantiomer of the title compound, which

출처 및 근거

ORD 기록
ord-bd4188ef75734ae48b736ca5adbdd175
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06911445B2

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