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Pyridine → methyl(E)-2-[[2-[2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvaleryl]hydrazino]sulphonamido]acetate

HRID 651826
ノート
印刷プレビュー

反応式

HRID 651826 の反応式
[C:1]([O:5][C:6]([C@H:8]([C@@H:18]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:19]([NH:21][NH2:22])=[O:20])[CH2:9]/[CH:10]=[CH:11]/[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[CH3:33][O:34][C:35](=[O:42])[CH2:36][NH:37][S:38](Cl)(=[O:40])=[O:39]>ClCCl.C(OCC)(=O)C>[C:1]([O:5][C:6]([C@H:8]([C@@H:18]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:19]([NH:21][NH:22][S:38]([NH:37][CH2:36][C:35]([O:34][CH3:33])=[O:42])(=[O:40])=[O:39])=[O:20])[CH2:9]/[CH:10]=[CH:11]/[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 1049PyridineHCID 14363949Ethyl 2-((chlorosulfonyl)amino)acetateHCID 69709501(E)-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvalerohydrazide

生成物 1

HCID 20681577methyl(E)-2-[[2-[2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvaleryl]hydrazino]sulphonamido]acetate収率 54.2%

試薬・触媒・溶媒 2

HCID 6344
Dichloromethane
溶媒
2 回
HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 1.08 g of (E)-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvalerohydrazide in 10 ml of dichloromethane was cooled to 0° C. under a nitrogen atmosphere and treated with 0.8 ml of pyridine and a solution of 1.5 g of N-(chlorosulphonyl)-glycine methyl ester in 5 ml of dichloromethane. The mixture was warmed to room temperature and stirred for 3 hours. The mixture was then diluted with ethyl acetate and washed with 2M aqueous hydrogen chloride and saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulphate and evaporated and the residue was purified by flash column chromatography on silica gel using hexane/ethyl acetate (3:2) for the elution to give 0.831 g of methyl(E)-2-[[2-[2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvaleryl]hydrazino]sulphonamido]acetate in the form of a solid.

後処理

  1. washwashed with 2M aqueous hydrogen chloride and saturated aqueous sodium chloride
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulphate
  3. customevaporated
  4. customthe residue was purified by flash column chromatography on silica gel
  5. washfor the elution

出典と根拠

ORDレコード
ord-57acf081124e431b929f1f1e9c0159f9
出典データセット
uspto-grants-2001_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06281363B1

反応ノート

読み込み中…

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