Phenol → HCID 68713043、化合物

HRID 451873

反応式

HRID 451873 の反応式
[Si:1]([O:8][CH2:9][CH:10]1[CH2:12][N@@:11]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:20]1([OH:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([O-])([O-])=O.[K+].[K+]>>[Si:1]([O:8][CH2:9][C@@H:10]([NH:11][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:12][O:26][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

参加物

4

反応物 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 72525716(S)-tert-butyl 2-(t-butyldimethylsilyloxymethyl)aziridine-1-carboxylate

生成物 1

HCID 68713043HCID 68713043、化合物収率 30%

実験手順

(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)aziridine-1-carboxylate (5.0 g, 17.4 mmol), phenol (4.92 g, 52.3 mmol), K2CO3 (24 g, 174 mmol) and 150 mL of acetonenitrile were mixed, and heated to reflux for 48 h. The mixture was filtrated, and the filtrate was concentrated in vacuo. The residue was dissolved in 100 mL of EA, which was washed with water (50 mL×2), brine (50 mL) and dried with Na2SO4. The solution was concentrated in vacuo to give crude product, which was purified with flash column to give (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-phenoxypropan-2-ylcarbamate (2.0 g, 5.2 mmol, yield 30%) 1H NMR (CDCl3, 400 MHz) δ 0.0 (s, 6H), 0.87 (s, 9H), 1.45 (s, 9H), 3.71 (dd, 1H), 3.85 (dd, 1H), 3.98 (d, 2H), 4.05 (s, 1H), 6.93 (m, 3H), 7.28 (m, 2H). MS ESI +ve m/z 382 (M+1).

後処理

  1. temperatureheated
  2. temperatureto reflux for 48 h
  3. filtrationThe mixture was filtrated
  4. concentrationthe filtrate was concentrated in vacuo
  5. dissolutionThe residue was dissolved in 100 mL of EA
  6. washwhich was washed with water (50 mL×2), brine (50 mL)
  7. dry with materialdried with Na2SO4
  8. concentrationThe solution was concentrated in vacuo
  9. customto give crude product, which
  10. customwas purified with flash column

出典と根拠

ORDレコード
ord-86c75eea12284324bc06835ca933da1c
出典データセット
uspto-grants-2013_07
特許番号
US08487108B2

関連ノート

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