Ethyl Acetate → (2R,3R)-2-(2,4-Difluorophenyl)-3-(1H-1,2,4-triazol-1-yl)-3-[[1-(tert-butoxycarbonyl)piperidin-4-yl]thio]-2-butanol

HRID 1601361

反応式

HRID 1601361 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([SH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[F:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[C@@:25]1([CH2:29][N:30]2[CH:34]=[N:33][CH:32]=[N:31]2)[C@H:27](C)[O:26]1.[C:35](OCC)(=O)C>CN(C)C=O>[F:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[C@@:25]([OH:26])([C@:29]([N:30]1[CH:34]=[N:33][CH:32]=[N:31]1)([S:14][CH:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]1)[CH3:35])[CH3:27]

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 101311911-((2-(2,4-Difluorophenyl)-3-methyloxiran-2-yl)methyl)-1H-1,2,4-triazole, (2R-cis)-HCID 21906090tert-Butyl 4-sulfanylpiperidine-1-carboxylate

生成物 1

HCID 53773004(2R,3R)-2-(2,4-Difluorophenyl)-3-(1H-1,2,4-triazol-1-yl)-3-[[1-(tert-butoxycarbonyl)piperidin-4-yl]thio]-2-butanol収率 53%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

In 6 ml of dimethylformamide was dissolved 1-(tert-butoxycarbonyl)-4-mercaptopiperidine (corresponding to 2 mmol) as described in Reference example 12, and 86 mg (1.97 mmol) of 55% sodium hydride were added to the solution at 0° C. under a nitrogen atmosphere, followed by stirring of the resulting mixture at the same temperature for 20 minutes. Then, 503 mg (2.00 mmol) of (2R,3S)-2-(2,4-difluorophenyl)-3-methyl-2-[(1H-1,2,4-triazol-1-yl)methyl]oxirane were added to the reaction mixture and the mixture was stirred at 60° C. for 3 hours. After cooling, ethyl acetate was added to the reaction mixture to dilute it and washed successively with water and a saturated aqueous NaCl solution. An oil obtained by evaporation of the solvent was subjected to silica gel column chromatography and eluted with ethyl acetate to obtain 557 mg (yield: 53%) of the desired compound as an oil.

後処理

  1. additionwere added to the solution at 0° C. under a nitrogen atmosphere
  2. stirringthe mixture was stirred at 60° C. for 3 hours
  3. temperatureAfter cooling
  4. additionto dilute it
  5. washwashed successively with water
  6. customAn oil obtained by evaporation of the solvent
  7. washeluted with ethyl acetate

出典と根拠

ORDレコード
ord-4b84ce05921c47c1b55748331cb6f5df
出典データセット
uspto-grants-1999_11
特許番号
US05977152

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