1-Bromo-5-isocyanatopentane → 1-(5-Bromopent-1-yl)-5-(3,4-difluorobenzyl)-2,3-dihydro-4-methoxycarbonyl-2(1H)-imidazolone

HRID 1003745노트

반응식

HRID 1003745 반응식
[CH3:1][O:2][C:3](=[O:17])[CH:4]([NH2:16])[C:5](=O)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([F:14])[CH:8]=1.[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][N:24]=[C:25]=[O:26]>O>[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][N:24]1[C:5]([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([F:13])=[C:9]([F:14])[CH:8]=2)=[C:4]([C:3]([O:2][CH3:1])=[O:17])[NH:16][C:25]1=[O:26]

참가 물질

4

반응물 2

HCID 144828831-Bromo-5-isocyanatopentaneHCID 54052828HCID 54052828, 화합물

생성물 1

HCID 187982741-(5-Bromopent-1-yl)-5-(3,4-difluorobenzyl)-2,3-dihydro-4-methoxycarbonyl-2(1H)-imidazolone수율 55%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To 2-amino-4-(3,4-difluorophenyl)-3-oxobutyric acid methyl ester (0.100 g, 0.344 mmol) in 2 mL water was added 1-bromo-5-isocyanatopentane (0.3 mL), and the reaction mixture refluxed for 3 hours. The reaction mixture was concentrated and partitioned between EtOAc (30 mL) and 1N HCl (10 mL). The organic layer was washed with saturated aqueous sodium bicarbonate solution (10 mL), dried over sodium sulfate, filtered and concentrated to give 0.080 g (55%) of the product as a syrup; 1H-NMR (CDCl3) δ1.36-1.81 (m, 6 H), 3.34 (t, J=6.6 Hz, 2 H), 3.32-3.37 (m, 2 H), 3.86 (s, 3 H), 4.21 (s, 2 H), 6.91-7.16 (m, 3 H), 9.53 (s, 1 H).

후처리

  1. temperaturethe reaction mixture refluxed for 3 hours
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned between EtOAc (30 mL) and 1N HCl (10 mL)
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution (10 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8496500ae94c465e81fb73771363abff
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06046331

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