2,4-Difluorobenzylamine → (1-Benzyl-3-{[3-(2,4-difluoro-benzylamino)-4-nitro-benzenesulfonyl]-isobutyl-amino}-2-hydroxy-propyl)-carbamic Acid hexahydro-furo[2,3-b]furan-3-yl Ester

HRID 660426노트

반응식

HRID 660426 반응식
[O:1]1[CH:5]2[O:6][CH2:7][CH2:8][CH:4]2[CH:3]([O:9][C:10](=[O:41])[NH:11][CH:12]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:13]([OH:33])[CH2:14][N:15]([S:20]([C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[C:25](F)[CH:24]=2)(=[O:22])=[O:21])[CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:2]1.[F:42][C:43]1[CH:50]=[C:49]([F:51])[CH:48]=[CH:47][C:44]=1[CH2:45][NH2:46]>O1CCCC1>[O:1]1[CH:5]2[O:6][CH2:7][CH2:8][CH:4]2[CH:3]([O:9][C:10](=[O:41])[NH:11][CH:12]([CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:13]([OH:33])[CH2:14][N:15]([S:20]([C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[C:25]([NH:46][CH2:45][C:44]3[CH:47]=[CH:48][C:49]([F:51])=[CH:50][C:43]=3[F:42])[CH:24]=2)(=[O:22])=[O:21])[CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:2]1

참가 물질

4

반응물 2

HCID 27332442,4-DifluorobenzylamineHCID 68508884{1-Benzyl-3-[(3-fluoro-4-nitro-benzenesulfonyl)-isobutyl-amino]-2-hydroxy-propyl}-carbamic Acid hexahydro-furo[2,3-b]furan-3-yl Ester

생성물 1

HCID 69155346(1-Benzyl-3-{[3-(2,4-difluoro-benzylamino)-4-nitro-benzenesulfonyl]-isobutyl-amino}-2-hydroxy-propyl)-carbamic Acid hexahydro-furo[2,3-b]furan-3-yl Ester수율 100%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

{1-Benzyl-3-[(3-fluoro-4-nitro-benzenesulfonyl)-isobutyl-amino]-2-hydroxy-propyl}-carbamic acid hexahydro-furo[2,3-b]furan-3-yl ester (7) (0.40 g, 0.67 mmol, 1 equiv) and 2,4-difluoro-benzylamine (0.14 g, 1 mmol, 1.49 equiv) were dissolved in tetrahydrofurane (10 mL). The solution was heated to reflux for 18 h. The solution was concentrated and the crude product was dissolved in dichloromethane (15 mL). The organic layer was washed with saturated NaHCO3 solution (15 mL). The organic layer was separated and evaporated under reduced pressure to yield the title compound (0.48 g, 0.67 mmol, quantitative). LRMS (ES+): m/z 719 [M+H]+.

후처리

  1. temperatureThe solution was heated
  2. temperatureto reflux for 18 h
  3. concentrationThe solution was concentrated
  4. dissolutionthe crude product was dissolved in dichloromethane (15 mL)
  5. washThe organic layer was washed with saturated NaHCO3 solution (15 mL)
  6. customThe organic layer was separated
  7. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-47dafd42dc0b4ea084f174b980f37af4
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084494B2

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