Succinic Acid → Succinic Acid

HRID 2090274

反応式

HRID 2090274 の反応式
[CH:1]1[CH:2]=[CH:3][C:4]([C@@H:7]2[N:16]([C:17]([O:19][C@@H:20]3[CH:25]4[CH2:26][CH2:27][N:22]([CH2:23][CH2:24]4)[CH2:21]3)=[O:18])[CH2:15][CH2:14][C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]2=3)=[CH:5][CH:6]=1.[C:28]([OH:35])(=[O:34])[CH2:29][CH2:30][C:31]([OH:33])=[O:32].C(O)(C)C>>[C:28]([OH:35])(=[O:34])[CH2:29][CH2:30][C:31]([OH:33])=[O:32].[CH:1]1[CH:6]=[CH:5][C:4]([C@@H:7]2[N:16]([C:17]([O:19][C@@H:20]3[CH:25]4[CH2:24][CH2:23][N:22]([CH2:27][CH2:26]4)[CH2:21]3)=[O:18])[CH2:15][CH2:14][C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]2=3)=[CH:3][CH:2]=1.[CH2:29]([C:28]([OH:35])=[O:34])[CH2:30][C:31]([OH:33])=[O:32]

参加物

5

反応物 3

HCID 1110Succinic AcidHCID 3776Isopropanol3 回HCID 154059Solifenacin2 回

生成物 2

HCID 1110Succinic AcidHCID 216457Solifenacin Succinate

実験手順

Crude oily solifenacin (35 g) obtained in Example 1 is dissolved in isopropanol (100 mL) at room temperature (20-24° C.). In a separate flask the solution of succinic acid (11.30 g, 95.55 mmol) in isopropanol (130 mL) is prepared at reflux for 5 min. The hot succinic acid solution is slowly added to the solifenacin solution in isopropanol. The resulting mixture is left to reach room temperature. At ca. 45° C. the mixture turned to be cloudy and white crystalline solid begins to precipitate. The solution is left at room temperature for 2 h 30 min. The crystalline solid is filtered off and washed with cold isopropanol (10° C.) (3×40 mL), then it is dried under reduced pressure (0.1-0.15 mmHg, room temperature, 2 h) to dry mass. After two steps solifenacin succinate is obtained in 38.9 g, (84.8%) yield, of purity (HPLC) 99.39%. The final product (38 g) is recrystallized in isopropanol (150 mL), yielding 34.4 g (90.7%) of solifenacin succinate of purity (HPLC) 99.71%; T(onset)≈150° C.

後処理

  1. temperatureat reflux for 5 min
  2. waitThe resulting mixture is left
  3. customto reach room temperature
  4. customAt ca. 45° C.
  5. customto precipitate
  6. filtrationThe crystalline solid is filtered off
  7. washwashed with cold isopropanol (10° C.) (3×40 mL)
  8. customit is dried under reduced pressure (0.1-0.15 mmHg, room temperature, 2 h)
  9. customto dry mass

出典と根拠

ORDレコード
ord-b54bb51777094ad4a4a18321e9a3e7fd
出典データセット
uspto-grants-2013_05
特許番号
US08436182B2

関連ノート

読み込み中…