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

HRID 1408313노트

반응식

HRID 1408313 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 7914Diisopropyl Ether용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-3f1860e48b584f17b7d850c8d8f6f019
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921355B2

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