Benzyl chloroformate → Tert-butyl 6-benzyloxycarbonylamino-3-(2-formylfuran-3-yl)-2-hydroxybenzoate

HRID 1778382ノート

反応式

HRID 1778382 の反応式
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH2:12][C:13]1[C:18]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[C:17]([OH:26])[C:16]([C:27]2[CH:31]=[CH:30][O:29][C:28]=2[CH:32]=[O:33])=[CH:15][CH:14]=1>C(OCC)C>[CH2:5]([O:4][C:2]([NH:12][C:13]1[C:18]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[C:17]([OH:26])[C:16]([C:27]2[CH:31]=[CH:30][O:29][C:28]=2[CH:32]=[O:33])=[CH:15][CH:14]=1)=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

参加物

4

反応物 2

HCID 10387Benzyl chloroformate2 回HCID 86684736Tert-butyl 6-amino-3-(2-formylfuran-3-yl)-2-hydroxybenzoate2 回

生成物 1

HCID 86684735Tert-butyl 6-benzyloxycarbonylamino-3-(2-formylfuran-3-yl)-2-hydroxybenzoate収率 47.7%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

Benzyl chloroformate (0.528 g) was added to a stirred solution of tert-butyl 6-amino-3-(2-formylfuran-3-yl)-2-hydroxybenzoate (Intermediate 61, 0.854 g) in diethyl ether (20 mL). The reaction mixture was stirred at room temperature for 2 hours. A further amount of benzyl chloroformate (1.056 g) was added and the resultant mixture stirred at room temperature overnight. The mixture was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane, with a gradient of 5-15% to give tert-butyl 6-benzyloxycarbonylamino-3-(2-formylfuran-3-yl)-2-hydroxybenzoate (0.588 g) as a yellow solid.

後処理

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified by chromatography on silica
  3. washeluting with a mixture of ethyl acetate and cyclohexane, with a gradient of 5-15%

出典と根拠

ORDレコード
ord-1633bd6ee271428da5f2d841afe23381
出典データセット
uspto-grants-2016_02
特許番号
US09266896B2

反応ノート

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