4-Nitrobenzenesulfonyl chloride → N-((4-Nitrophenyl)sulfonyl)-1-(tert-butyloxycarbonyl)piperazine

HRID 1841920노트

반응식

HRID 1841920 반응식
C(N(C(C)C)CC)(C)C.[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].[N+:23]([C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1)([O-:25])=[O:24]>C(Cl)Cl>[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][N:20]([S:32]([C:29]2[CH:28]=[CH:27][C:26]([N+:23]([O-:25])=[O:24])=[CH:31][CH:30]=2)(=[O:33])=[O:34])[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:11])[CH3:12]

참가 물질

5

반응물 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylate

생성물 1

HCID 10595407N-((4-Nitrophenyl)sulfonyl)-1-(tert-butyloxycarbonyl)piperazine수율 97.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Diisopropylethylamine (7.8 ml, 45 mmol) was added in one portion to a stirred solution of piperazine-1-carboxylic acid tert-butyl ester (7.6 g, 41 mmol) in DCM (100 ml) at room temperature. To this mixture was added 4-nitrophenyl sulfonyl chloride (10.0 g, 45 mmol) in one portion and the mixture was stirred at room temperature under a nitrogen atmosphere for 1 hour. After this time the mixture was diluted with DCM (50 ml) and washed with water (100 ml), saturated NaHCO3 (100 ml) and HCl (100 ml, 2M). The organic layer was separated, dried (MgSO4), filtered and concentrated under vacuum to give the title compound (14.9 g, 89% yield) as a white solid. δH (500 MHz, DMSO) 8.45 (2H, d), 7.97 (2H, d), 3.34 (4H, obscured), 2.96-2.92 (4H, m), 1.33 (9H, s). Tr=1.91 min m/z (ES+) ([(M−100)+H]+) 272.

후처리

  1. washwashed with water (100 ml), saturated NaHCO3 (100 ml) and HCl (100 ml, 2M)
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-242135966e4c4d0d9825c7fd476cb49c
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946197B2

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