(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 388450ノート

反応式

HRID 388450 の反応式
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

参加物

4

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
60 °C

実験手順

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+)

後処理

  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

出典と根拠

ORDレコード
ord-9cb3b996d5fd410fa90987cfd5656a9e
出典データセット
uspto-grants-2013_02
特許番号
US08377949B2

反応ノート

読み込み中…