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

HRID 1003745ノート

反応式

HRID 1003745 の反応式
[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]

参加物

4

反応物 2

HCID 144828831-Bromo-5-isocyanatopentaneHCID 54052828HCID 54052828、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8496500ae94c465e81fb73771363abff
出典データセット
uspto-grants-2000_04
特許番号
US06046331

反応ノート

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