4-Methylmorpholine → 2-[1(S)-{(1,1-Dimethylethoxy)carbonylamino}-2-phenylethyl]-1-(2-oxo-butyl)-4-phenyl-1H-imidazole

HRID 23369

反応式

HRID 23369 の反応式
[CH3:1][C:2]([CH3:27])([O:4][C:5]([NH:7][C@H:8]([C:16]1[NH:17][CH:18]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:20]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:6])[CH3:3].CN1CCOCC1.Br[CH2:36][C:37](=[O:40])[CH2:38][CH3:39]>CN(C=O)C>[CH3:3][C:2]([CH3:27])([O:4][C:5]([NH:7][C@H:8]([C:16]1[N:17]([CH2:36][C:37](=[O:40])[CH2:38][CH3:39])[CH:18]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:20]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:6])[CH3:1]

参加物

5

反応物 3

HCID 79724-MethylmorpholineHCID 131561-Bromo-2-butanoneHCID 178454143HCID 178454143、化合物

生成物 1

HCID 207565832-[1(S)-{(1,1-Dimethylethoxy)carbonylamino}-2-phenylethyl]-1-(2-oxo-butyl)-4-phenyl-1H-imidazole収率 90%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
20 °C

実験手順

To a solution of 2-[1(S)-{(1,1-dimethylethoxy)carbonylamino}-2-phenylethyl]4-phenyl-1H-imidazole (100 mg, 1 eq) in DMF (2 mL) were successively added morpholinomethyl polystyrene resin (Novabiochem, loading: 3.51 mmol/g, 159 mg, 2 eq) and 1-bromo-2-butanone (28 mL, 2 eq). After about 18 hours of stirring at about 20° C., 2 mL DMF were added to the reaction mixture followed by aminomethylpolystyrene resin (Novabiochem, loading: 1.73 mmol/g, 319 mg). The mixture was stirred overnight at 20° C. and filtered. The filtrate was concentrated under reduced pressure and then purified by a rapid filtration on a silica gel pad (Alltech silica cartridges) with ethylacetate as eluent to yield 107 mg (90% yield) of the title compound. NMR (1H, 400 MHz, CDCl3) δ: 7.80-6.98 (m, 11H, arom. H), 5.45 (d, 1H, NH), 4.80 (m, 1H, CH), 4.40 (AB, J=18 Hz, NCH2CO), 3.33 (m, 2H, CH2Ph), 2.25 (m, 2H, CH2CH3), 1.0 (t, 3H, CH3). LC/MS: calculated MW=433.5, m/z=434.2 (M+H), m/z=432.2 (M−H).

後処理

  1. stirringThe mixture was stirred overnight at 20° C.
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. filtrationpurified by a rapid filtration on a silica gel pad (Alltech silica cartridges) with ethylacetate as eluent

出典と根拠

ORDレコード
ord-414f20ffe5e343bebd38fc47bf8f8ed5
出典データセット
uspto-grants-2005_02
特許番号
US06852725B1

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