Phenethylamine → [1-(5-Phenethylcarbamoyl-furan-2-sulfonyl)-piperidin-4-yl]-carbamic acid tert-butyl ester

HRID 337227노트

반응식

HRID 337227 반응식
[CH2:1]([NH2:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C[O:11][C:12]([C:14]1[O:15][C:16]([S:19]([N:22]2[CH2:27][CH2:26][CH:25]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:24][CH2:23]2)(=[O:21])=[O:20])=[CH:17][CH:18]=1)=O>CO>[C:32]([O:31][C:29](=[O:30])[NH:28][CH:25]1[CH2:26][CH2:27][N:22]([S:19]([C:16]2[O:15][C:14]([C:12](=[O:11])[NH:9][CH2:1][CH2:2][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)=[CH:18][CH:17]=2)(=[O:21])=[O:20])[CH2:23][CH2:24]1)([CH3:35])([CH3:33])[CH3:34]

참가 물질

4

반응물 2

HCID 1001PhenethylamineHCID 710601525-(4-tert-Butoxycarbonylamino-piperidine-1-sulfonyl)-furan-2-carboxylic acid methyl ester

생성물 1

HCID 71060234[1-(5-Phenethylcarbamoyl-furan-2-sulfonyl)-piperidin-4-yl]-carbamic acid tert-butyl ester수율 96.3%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
45 °C

실험 절차

Phenethylamine (0.5 g, 4.1 mmol) was added in one portion to a stirred solution of 5-(4-tert-butoxycarbonylamino-piperidine-1-sulfonyl)-furan-2-carboxylic acid methyl ester (0.4 g, 1.0 mmol) in methanol (10 ml) at room temperature. The reaction mixture was then heated to 45° C. and stirred at this temperature overnight, after which time the mixture was concentrated. The resulting residue was dissolved in DCM (100 ml), 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 to give the title compound (0.46 g, 94% yield) as a light brown solid which was taken on without further purification. δH (500 MHz, DMSO) 8.71 (t, J=5.79 Hz, 1 H) 7.13-7.38 (m, 8 H) 6.93 (d, J=7.61 Hz, 1 H) 5.75 (s, 1 H) 3.41-3.63 (m, 5 H) 2.66-2.91 (m, 5 H) 1.66-1.87 (m, 2 H) 1.25-1.47 (m, 12 H).

후처리

  1. concentrationafter which time the mixture was concentrated
  2. dissolutionThe resulting residue was dissolved in DCM (100 ml)
  3. washwashed sequentially with HCl (1M solution, 50 ml), NaOH (1M solution, 50 ml) and brine (50 ml)
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e5ab40a0643946b2a0a8bbd481e2ef52
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889716B2

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