N-(tert-Butoxycarbonyl)-1,5-diaminopentane → Tert-butyl 5-(2-nitrophenylsulfonamido)pentylcarbamate

HRID 1408313ノート

反応式

HRID 1408313 の反応式
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11].[N+:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[S:24](Cl)(=[O:26])=[O:25])([O-:17])=[O:16].C(N(C(C)C)CC)(C)C>C(Cl)Cl.C(OC(C)C)(C)C>[N+:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[S:24]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])(=[O:26])=[O:25])([O-:17])=[O:16]

参加物

6

反応物 3

HCID 4352N-(tert-Butoxycarbonyl)-1,5-diaminopentaneHCID 155402-Nitrobenzenesulfonyl chlorideHCID 81531Diisopropylethylamine

生成物 1

HCID 67226448Tert-butyl 5-(2-nitrophenylsulfonamido)pentylcarbamate収率 85%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 7914Diisopropyl Ether溶媒

実験手順

To a solution of tert-butyl 5-aminopentylcarbamate 30a (20 g, 99 mmoles) and 2-nitrobenzene-1-sulfonyl chloride 30b (23 g, 1.05 eq) in DCM (200 mL) was added dropwise diisopropyl ethyl amine (19.2 g, 1.5 eq) at 0° C. After stirring at RT overnight, the RM was successively washed with an aqueous solution of citric acid, then brine, dried over magnesium sulfate, filtered and concentrated. Trituration in diisopropyl ether afforded 32.61 g (85% yield) of tert-butyl 5-(2-nitrophenylsulfonamido)pentylcarbamate 30c as a white solid; m/z 388 [M+H]+.

後処理

  1. washthe RM was successively washed with an aqueous solution of citric acid
  2. dry with materialbrine, dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-3f1860e48b584f17b7d850c8d8f6f019
出典データセット
uspto-grants-2014_12
特許番号
US08921355B2

反応ノート

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