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Water → tert-butyl{(2S)-1-[4-chloro-2-(1,1,1-trifluoro-2-methylpropan-2-yl)phenoxy]propan-2-yl}carbamate

HRID 2178701
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HRID 2178701 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([C:15]([CH3:21])([CH3:20])[C:16]([F:19])([F:18])[F:17])[CH:9]=1.CS(O[CH2:27][C@@H:28]([NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH3:29])(=O)=O.O>CN(C)C=O>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:29][C@@H:28]([NH:30][C:31](=[O:32])[O:33][C:34]([CH3:35])([CH3:37])[CH3:36])[CH3:27])=[C:10]([C:15]([CH3:21])([CH3:20])[C:16]([F:17])([F:18])[F:19])[CH:9]=1
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6

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HCID 962WaterHCID 10796Cesium carbonateHCID 10753379(S)-Methanesulphonic acid 2-Boc-aminopropyl esterHCID 866717284-Chloro-2-(1,1,1-trifluoro-2-methylpropan-2-yl)phenol

생성물 1

HCID 70807897tert-butyl{(2S)-1-[4-chloro-2-(1,1,1-trifluoro-2-methylpropan-2-yl)phenoxy]propan-2-yl}carbamate

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

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온도
60 °C

실험 절차

Cesium carbonate (2.05 g, 6.28 mmol) was added to a solution of 4-chloro-2-(1,1,1-trifluoro-2-methylpropan-2-yl)phenol (C48) (500 mg, 2.10 mmol) in N,N-dimethylformamide (5 mL). (2S)-2-[(tert-Butoxycarbonyl)amino]propyl methanesulfonate (P12) (0.53 g, 2.1 mmol) was added, and the reaction mixture was heated to 60° C. After 30 minutes, additional P12 (0.53 g, 2.1 mmol) was added, and heating was continued for 18 hours. Water (100 mL) was added, and the mixture was extracted with diethyl ether (3×50 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Silica gel chromatography (Gradient: 0% to 15% ethyl acetate in heptane) afforded the product as a colorless oil. Yield: 625 mg, 1.58 mmol, 75%.

후처리

  1. additionadditional P12 (0.53 g, 2.1 mmol) was added
  2. temperatureheating
  3. waitwas continued for 18 hours
  4. extractionthe mixture was extracted with diethyl ether (3×50 mL)
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-eb8cedd37a054055b331dcec2b8eb380
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09067934B2

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