Benzyl chloroformate → benzyl {(1S)-1-[2-bromo-5-(trifluoromethyl)phenyl]pent-4-en-1-yl}carbamate

HRID 529705노트

반응식

HRID 529705 반응식
CCN(C(C)C)C(C)C.[Br:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:12]=1[C@@H:21]([NH2:26])[CH2:22][CH2:23][CH:24]=[CH2:25].Cl[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29]>C(Cl)Cl>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:19])([F:20])[F:18])=[CH:13][C:12]=1[C@@H:21]([NH:26][C:28](=[O:29])[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:22][CH2:23][CH:24]=[CH2:25]

참가 물질

5

반응물 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 86682269(1S)-1-[2-bromo-5-(trifluoromethyl)phenyl]pent-4-en-1-amine

생성물 1

HCID 86682268benzyl {(1S)-1-[2-bromo-5-(trifluoromethyl)phenyl]pent-4-en-1-yl}carbamate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To DIPEA (7.48 mL, 42.8 mmol) and (1S)-1-[2-bromo-5-(trifluoromethyl)phenyl]pent-4-en-1-amine (4.4 g, 14.3 mmol) in DCM (20 mL) was added benzyl chloroformate at 0° C. The reaction was stirred at room temperature for 2 hours and was quenched with water. The organic was washed with 10% aqueous KOH and the aqueous was back-extracted with ethyl acetate. The combined organics were dried over sodium sulfate, filtered, concentrated and then purified by column chromatography to yield benzyl {(1S)-1-[2-bromo-5-(trifluoromethyl)phenyl]pent-4-en-1-yl}carbamate (5.8 g, 13.1 mmol). 1H NMR (500 MHz, CDCl3) δ7.72 (m, 1H), 7.58 (s, 1H), 7.39 (b, 5H), 7.1 (m, 1H), 5.83 (m, 1H), 5.3 (b, 1H), 5.15 (m, 3H), 2.22 (m, 1H), 2.18 (m, 1H), 1.95 (m, 1H), 1.78 (m, 1H).

후처리

  1. customwas quenched with water
  2. washThe organic was washed with 10% aqueous KOH
  3. extractionthe aqueous was back-extracted with ethyl acetate
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-aff426b2b0ed48f28ee2c387839db251
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346825B2

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