Benzyl chloroformate → 7-Methoxy-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepine-4-carboxylic acid benzyl ester

HRID 1687944노트

반응식

HRID 1687944 반응식
C([N:8]1[CH2:14][C:13]2[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=[CH:18][C:12]=2[NH:11][C:10](=[O:21])[CH2:9]1)C1C=CC=CC=1.Cl[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]>ClCCl>[CH2:26]([O:25][C:23]([N:8]1[CH2:14][C:13]2[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=[CH:18][C:12]=2[NH:11][C:10](=[O:21])[CH2:9]1)=[O:24])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

참가 물질

4

반응물 2

HCID 10387Benzyl chloroformateHCID 578538974-Benzyl-7-methoxy-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one

생성물 1

HCID 672637677-Methoxy-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepine-4-carboxylic acid benzyl ester수율 93%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-benzyl-7-methoxy-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one (4.67 g, 16.5 mmol) in dichloromethane (150 mL) was added benzyl chloroformate (6.2 g, 36.0 mmol). The mixture was heated to reflux for four hours whereupon LCMS showed completion of the reaction. The mixture was cooled to room temperature, washed with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered and concentrated. The crude product was purified by flash chromatography over silica gel (0-5% MeOH/DCM) to afford 5.0 g (93%) of 7-methoxy-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepine-4-carboxylic acid benzyl ester; NMR (400 MHz, DMSO-d6) δ 9.96 (s, 1H), 7.35 (m, 5H), 7.04 (d, J=9 Hz, 1H), 6.84 (d, J=9 Hz, 1H), 5.08 (s, 2H), 4.54 (s, 2H), 4.20 (2s, 2H), 3.70 (2s, 3H); MS (m/e) 327 (M+1); mp 138° C.

후처리

  1. temperatureThe mixture was heated
  2. temperatureto reflux for four hours whereupon LCMS
  3. customcompletion of the reaction
  4. washwashed with saturated aqueous sodium bicarbonate and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by flash chromatography over silica gel (0-5% MeOH/DCM)

출처 및 근거

ORD 기록
ord-70d890e25a014b618fdbdde14dc8121a
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148391B2

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