Triethylamine → 2-[4-[2-(benzoxazol-2-ylthio)ethyl]-piperazin-1-yl]-N-(2,6-diisopropyl-3-mesyloxyphenyl)acetamide

HRID 1064807ノート

反応式

HRID 1064807 の反応式
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[O:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[S:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]([NH:27][C:28]2[C:33]([CH:34]([CH3:36])[CH3:35])=[CH:32][CH:31]=[C:30]([OH:37])[C:29]=2[CH:38]([CH3:40])[CH3:39])=[O:26])[CH2:20][CH2:19]1.C(N(CC)CC)C>C1COCC1.O>[O:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[S:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]([NH:27][C:28]2[C:33]([CH:34]([CH3:35])[CH3:36])=[CH:32][CH:31]=[C:30]([O:37][S:2]([CH3:1])(=[O:4])=[O:3])[C:29]=2[CH:38]([CH3:40])[CH3:39])=[O:26])[CH2:20][CH2:19]1

参加物

6

反応物 3

HCID 8471Triethylamine2 回HCID 31297Methanesulfonyl chloride2 回HCID 222726162-[4-[2-(benzoxazol-2-ylthio)ethyl]piperazin-1-yl]-N-(2,6-diisopropyl-3-hydroxyphenyl)acetamide

生成物 1

HCID 222727962-[4-[2-(benzoxazol-2-ylthio)ethyl]-piperazin-1-yl]-N-(2,6-diisopropyl-3-mesyloxyphenyl)acetamide収率 70%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Methanesulfonyl chloride (103 mg, 0.9 mmol) was added to a solution of 2-[4-[2-(benzoxazol-2-ylthio)ethyl]piperazin-1-yl]-N-(2,6-diisopropyl-3-hydroxyphenyl)acetamide (149 mg, 0.3 mmol) and triethylamine (91 mg, 0.9 mmol) in THF (2 ml) with ice-cooling and the mixture was stirred for 30 minutes. Then triethylamine (46 mg, 0.45 mmol) and methanesulfonyl chloride (52 mg, 0.45 mmol) were further added thereto and the mixture was stirred for 20 minutes. The reaction solution was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride solution successively and dried over sodium sulfate and the solvent was evaporated therefrom. The residue was purified by a silica gel column chromatography (20 g of silica gel; developing solvent, chloroform:methanol=20:1) and the resulting crude crystals were recrystallized from acetone and hexane to provide 120 mg (yield 70%) of the desired compound as colorless crystals.

後処理

  1. temperaturecooling
  2. stirringthe mixture was stirred for 20 minutes
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materiala saturated sodium chloride solution successively and dried over sodium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was purified by a silica gel column chromatography (20 g of silica gel; developing solvent, chloroform:methanol=20:1)
  8. customthe resulting crude crystals were recrystallized from acetone and hexane

出典と根拠

ORDレコード
ord-cd1215c8721448ccbb160dc4707abdb8
出典データセット
uspto-grants-2005_11
特許番号
US06969711B2

反応ノート

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