Water → (+/-)-Acetic acid (2RS,4aRS,10bRS)-6-(4-butoxy-phenyl)-8,9-dimethoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-yl ester

HRID 2054428

反応式

HRID 2054428 の反応式
P(Cl)(Cl)(Cl)(Cl)Cl.[CH2:7]([O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([NH:20][CH:21]2[CH2:26][CH2:25][CH:24]([O:27][C:28](=[O:30])[CH3:29])[CH2:23][CH:22]2[C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[C:33]([O:39][CH3:40])[CH:32]=2)=O)=[CH:14][CH:13]=1)[CH2:8][CH2:9][CH3:10].C(N(CC)CC)C.O>ClCCl>[CH2:7]([O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:36]3[C:31](=[CH:32][C:33]([O:39][CH3:40])=[C:34]([O:37][CH3:38])[CH:35]=3)[CH:22]3[CH:21]([CH2:26][CH2:25][CH:24]([O:27][C:28](=[O:30])[CH3:29])[CH2:23]3)[N:20]=2)=[CH:14][CH:13]=1)[CH2:8][CH2:9][CH3:10]

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 24819Phosphorus pentachlorideHCID 86601276(+/-)-Acetic acid (1RS,3RS,4RS)-4-{[1-(4-butoxy-phenyl)-methanoyl]-amino}-3-(3,4-dimethoxy-phenyl)-cyclohexyl ester2 回

生成物 1

HCID 10433966(+/-)-Acetic acid (2RS,4aRS,10bRS)-6-(4-butoxy-phenyl)-8,9-dimethoxy-1,2,3,4,4a,10b-hexahydrophenanthridin-2-yl ester収率 87.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

1670 mg of phosphorous pentachloride are suspended in 2.5 ml of dichloromethane. 1119 mg of (±)-acetic acid (1RS,3RS,4RS)-4-{[1-(4-butoxy-phenyl)-methanoyl]-amino}-3-(3,4dimethoxy-phenyl)-cyclohexyl ester (compound A7) dissolved in 15 ml of dichloromethane are added and the mixture stirred for 18 h. The mixture is cooled to 0° C. and 10 ml of triethylamine added, then 5 ml of water. After phase separation and removal of solvent the solid residue is purified by flash chromatography [silica, toluene/dioxane=2:1 (containing 0.5% of ammonia)] to give 940 mg of the title compound as a colorless foam (87% of theory).

後処理

  1. additionare added
  2. customAfter phase separation and removal of solvent the solid residue
  3. customis purified by flash chromatography [silica, toluene/dioxane=2:1 (containing 0.5% of ammonia)]

出典と根拠

ORDレコード
ord-28140030001e41aabfacb7e982e2c1dd
出典データセット
uspto-grants-2008_02
特許番号
US07329676B2

関連ノート

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