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

HRID 1778382노트

반응식

HRID 1778382 반응식
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

참가 물질

4

반응물 2

HCID 10387Benzyl chloroformate2회HCID 86684736Tert-butyl 6-amino-3-(2-formylfuran-3-yl)-2-hydroxybenzoate2회

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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.

후처리

  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%

출처 및 근거

ORD 기록
ord-1633bd6ee271428da5f2d841afe23381
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266896B2

반응 노트

불러오는 중…