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 660426ノート

反応式

HRID 660426 の反応式
[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

参加物

4

反応物 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

生成物 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 Ester収率 100%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

{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]+.

後処理

  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

出典と根拠

ORDレコード
ord-47dafd42dc0b4ea084f174b980f37af4
出典データセット
uspto-grants-2011_12
特許番号
US08084494B2

反応ノート

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