Benzyl chloroformate → [4-(4-Acryloylamino-piperidine-1-sulfonyl)-phenyl]carbamic acid benzyl ester

HRID 337202노트

반응식

HRID 337202 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][CH:14]([NH:17][C:18](=[O:21])[CH:19]=[CH2:20])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.Cl[C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33]>C1COCC1.C(Cl)Cl>[CH2:35]([O:34][C:32](=[O:33])[NH:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]2[CH2:12][CH2:13][CH:14]([NH:17][C:18](=[O:21])[CH:19]=[CH2:20])[CH2:15][CH2:16]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

참가 물질

6

반응물 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 71618273N-[1-(4-Amino-benzenesulfonyl)-piperidin-4-yl]-acrylamide

생성물 1

HCID 71449433[4-(4-Acryloylamino-piperidine-1-sulfonyl)-phenyl]carbamic acid benzyl ester수율 34%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

N-[1-(4-Amino-benzenesulfonyl)-piperidin-4-yl]-acrylamide (0.09 g, 0.3 mmol) was dissolved in THF (5 ml). To this was added diisopropylethylamine (0.1 ml, 0.6 mmol) in one portion followed by the drop wise addition of benzyl chloroformate (0.05 ml, 0.33 mmol) and the mixture was stirred at room temperature under a nitrogen atmosphere for 3 hours. After this time the mixture was diluted with DCM (100 ml) and washed sequentially with HCl (1M solution, 50 ml), NaOH (1M solution, 50 ml) and brine (50 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated. The resulting residue was purified by flash column chromatography (elution: 100% EtOAc) to give the title compound (0.04 g, 34% yield) as a white powder.

후처리

  1. washwashed sequentially with HCl (1M solution, 50 ml), NaOH (1M solution, 50 ml) and brine (50 ml)
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified by flash column chromatography (elution: 100% EtOAc)

출처 및 근거

ORD 기록
ord-c8d40014bebf4708ad8cc61cd3084959
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889716B2

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