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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
ノート
印刷プレビュー

反応式

HRID 2178701 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
60 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-eb8cedd37a054055b331dcec2b8eb380
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09067934B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート