ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Sodium Thiosulfate → (2R)-2-Allyloxycarbonylamino-2-methyl-4-[5-(4-cyclohexyloxybut-1-ynyl)furan-2-yl]-1-butyl diallyl phosphate

HRID 422914
ノート
印刷プレビュー

反応式

HRID 422914 の反応式
[CH2:1]([O:4][C:5]([NH:7][C@:8]([CH3:29])([CH2:11][CH2:12][C:13]1[O:14][C:15]([C:18]#[C:19][CH2:20][CH2:21][O:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:16][CH:17]=1)[CH2:9][OH:10])=[O:6])[CH:2]=[CH2:3].N1C=NN=N1.C(N(C(C)C)[P:39]([O:44][CH2:45][CH:46]=[CH2:47])[O:40][CH2:41][CH:42]=[CH2:43])(C)C.ClC1C=CC=C(C(OO)=[O:59])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[P:39]([O:40][CH2:41][CH:42]=[CH2:43])([O:44][CH2:45][CH:46]=[CH2:47])([O:10][CH2:9][C@@:8]([NH:7][C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])([CH3:29])[CH2:11][CH2:12][C:13]1[O:14][C:15]([C:18]#[C:19][CH2:20][CH2:21][O:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:16][CH:17]=1)=[O:59]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 4686855Diallyl diisopropylphosphoramiditeHCID 66673269(2R)-2-Allyloxycarbonylamino-2-methyl-4-[5-(4-cyclohexyloxybut-1-ynyl) furan-2-yl]butan-1-olHCID 178418441HCID 178418441、化合物

生成物 1

HCID 66672845
(2R)-2-Allyloxycarbonylamino-2-methyl-4-[5-(4-cyclohexyloxybut-1-ynyl)furan-2-yl]-1-butyl diallyl phosphate
収率 81.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (2R)-2-allyloxycarbonylamino-2-methyl-4-[5-(4-cyclohexyloxybut-1-ynyl)furan-2-yl]butan-1-ol (0.6202 g, 1.54 mmol) obtained in Example (26a) in dichloromethane (15 ml) were added successively 1H-tetrazole (0.7220 g, 10.31 mmol) and diallyl diisopropylphosphoramidite (0.81 ml, 3.06 mmol) with stirring under ice-cooling, and then the reaction mixture was stirred at room temperature for 2 hours. After stirring, to the reaction mixture was added m-chloroperbenzoic acid (content: 70%) (0.7556 g, 3.07 mmol) with stirring under ice cooling, and the resulting mixture was stirred at the same temperature for 10 minutes. After stirring, to the reaction mixture was added 10% aqueous sodium thiosulfate solution to quench the reaction, and the resulting mixture was extracted with dichloromethane. The extract was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. After filtration, the solvent was removed in vacuo, and the residue was purified by chromatography on a silica gel-column using a mixed solvent of hexane and ethyl acetate (3:2) as the eluent to afford the title compound (0.7049 g, yield: 81%).

後処理

  1. temperaturecooling
  2. stirringthe reaction mixture was stirred at room temperature for 2 hours
  3. stirringAfter stirring, to the reaction mixture
  4. stirringwith stirring under ice cooling
  5. stirringthe resulting mixture was stirred at the same temperature for 10 minutes
  6. stirringAfter stirring, to the reaction mixture
  7. customto quench
  8. customthe reaction
  9. extractionthe resulting mixture was extracted with dichloromethane
  10. washThe extract was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution
  11. dry with materialdried over anhydrous sodium sulfate
  12. filtrationAfter filtration
  13. customthe solvent was removed in vacuo
  14. customthe residue was purified by chromatography on a silica gel-column

出典と根拠

ORDレコード
ord-afc244cafe4a4fee928089802f73c6ce
出典データセット
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08101650B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート