Methanesulfonyl chloride → (S)-3-(tert-butoxycarbonylamino)-4-(4-chlorophenyl)butyl methanesulfonate

HRID 598885

반응식

HRID 598885 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@H:9]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:10][CH2:11][OH:12])=[CH:4][CH:3]=1.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl>[CH3:21][S:22]([O:12][CH2:11][CH2:10][C@@H:9]([NH:13][C:14]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:20])[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:24])=[O:23]

참가 물질

4

반응물 2

HCID 31297Methanesulfonyl chlorideHCID 57950531(S)-tert-Butyl 1-(4-chlorophenyl)-4-hydroxybutan-2-ylcarbamate

생성물 1

HCID 57950570(S)-3-(tert-butoxycarbonylamino)-4-(4-chlorophenyl)butyl methanesulfonate수율 94%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a mixture of (S)-tert-Butyl 1-(4-chlorophenyl)-4-hydroxybutan-2-ylcarbamate (686 mg, 2.3 mmol) and TEA (399 μl, 2.9 mmol) in DCM (10 mL) at −8° C. was added methanesulfonyl chloride (214 μl, 2.7 mmol). The resulting mixture was stirred for 2 hours. After warming to room temperature, the mixture was diluted with DCM and washed with H2O (2×). The combined organic layers were dried over Na2SO4, filtered, and concentrated to give the product as a light yellow solid (815 mg, 94%). LCMS (API-ES) m/z: 400 (M+Na+).

후처리

  1. washwashed with H2O (2×)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-212a2d19de924ef1afb40824f29da493
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897619B2

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