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

HRID 23369

반응식

HRID 23369 반응식
[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]

참가 물질

5

반응물 3

HCID 79724-MethylmorpholineHCID 131561-Bromo-2-butanoneHCID 178454143HCID 178454143, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
20 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-414f20ffe5e343bebd38fc47bf8f8ed5
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06852725B1

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