(R)-cyclohexyl-[1-(1,4-dimethyl-1H-indol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-acetic acid methyl ester → (R)-Cyclohexyl-[1-(1,4-dimethyl-1H-indol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-acetic acid

HRID 388450노트

반응식

HRID 388450 반응식
C[O:2][C:3](=[O:35])[C@@H:4]([CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)[N:5]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:16][C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][C:24]=3[CH3:26])[N:19]([CH3:27])[CH:18]=2)[C:6]1=[O:28]>O1CCOCC1.O>[CH:29]1([C@@H:4]([N:5]2[C:14](=[O:15])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([CH2:16][C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][C:24]=4[CH3:26])[N:19]([CH3:27])[CH:18]=3)[C:6]2=[O:28])[C:3]([OH:35])=[O:2])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

참가 물질

4

반응물 1

HCID 68743060(R)-cyclohexyl-[1-(1,4-dimethyl-1H-indol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-acetic acid methyl ester

생성물 1

HCID 25191733(R)-Cyclohexyl-[1-(1,4-dimethyl-1H-indol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-acetic acid

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
60 °C

실험 절차

To a solution of (R)-cyclohexyl-[1-(1,4-dimethyl-1H-indol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl]-acetic acid methyl ester (124 mg, 0.26 mmol) in dioxane (2.5 ml) is added a solution of LiOH monohydrate (25 mg, 0.60 mmol) in H2O (2.5 mL). The solution is stirred at 60° C. for 16 hours. The reaction mixture is allowed to cool to room temperature, quenched with 4M HCl in dioxane (500 μL) and is concentrated. The resulting residue is purified by flash chromatography with 3.5% MeOH in dichloromethane as the eluent to afford the title compound. LCMS (ESMS): m/z 460.86 (M+H+)

후처리

  1. temperatureto cool to room temperature
  2. customquenched with 4M HCl in dioxane (500 μL)
  3. concentrationis concentrated
  4. customThe resulting residue is purified by flash chromatography with 3.5% MeOH in dichloromethane as the eluent

출처 및 근거

ORD 기록
ord-9cb3b996d5fd410fa90987cfd5656a9e
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08377949B2

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