Sodium hydride → HCID 22873045、化合物

HRID 1781956ノート

反応式

HRID 1781956 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:10][OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[F:27][C:28]([F:42])([F:41])[C:29]1[CH:30]=[C:31]([CH:34]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:36]=1)[CH2:32]Br>O1CCCC1.CN(C)C=O>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH:12]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH2:10][O:11][CH2:32][C:31]1[CH:34]=[C:35]([C:37]([F:39])([F:40])[F:38])[CH:36]=[C:29]([C:28]([F:27])([F:41])[F:42])[CH:30]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 1225733,5-Bis(trifluoromethyl)benzyl bromideHCID 16213633(S)-tert-Butyl (3-hydroxy-1,1-diphenylpropan-2-yl)carbamate

生成物 1

HCID 22873045HCID 22873045、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a cooled solution (0° C.) of (S)-2-t-butoxycarbonylamino-3,3-diphenylpropan-1-ol (2.04 g, 6.2 mmol, Example 1 g) in tetrahydrofuran (50 ml) and dimethylformamide (10 ml) was added sodium hydride (0.187 g, 80% suspension in oil) over 15 minutes. After an additional 10 minutes 3,5-bis(trifluoromethyl)benzyl bromide (1.14 ml) was added and the solution stirred at room temperature for 16 h. The solvent was removed in vacuo and the residue partitioned between CH2Cl2 and water. After washing the organic phase with saturated brine and drying (MgSO4), the solvent was removed in vacuo and the residue chromatographed on silica gel in ethyl acetate/hexane (0:100 to 50:50) to give (S)-2-t-butoxycarbonylamino-1-((3.5bis(trifluoromethyl)phenyl)methyloxy)3,3-diphenylpropane, 2.92 g.

後処理

  1. customover 15 minutes
  2. customThe solvent was removed in vacuo
  3. customthe residue partitioned between CH2Cl2 and water
  4. washAfter washing the organic phase with saturated brine
  5. dry with materialdrying (MgSO4)
  6. customthe solvent was removed in vacuo
  7. customthe residue chromatographed on silica gel in ethyl acetate/hexane (0:100 to 50:50)

出典と根拠

ORDレコード
ord-3592964bb411464a9d252afbb2f06a56
出典データセット
uspto-grants-1997_05
特許番号
US05633281

反応ノート

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