(RS)-Clopidogrel → 2-chlorophenyl(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetic acid methyl ester (-)-camphorsulfonic acid salt

HRID 323893

反応式

HRID 323893 の反応式
[CH3:1][O:2][C:3](=[O:21])[CH:4]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:20])[N:5]1[CH2:10][CH2:9][C:8]2[S:11][CH:12]=[CH:13][C:7]=2[CH2:6]1.O.[C:23]12([CH2:33][S:34]([OH:37])(=[O:36])=[O:35])[C:30]([CH3:32])([CH3:31])[CH:27]([CH2:28][CH2:29]1)[CH2:26][C:24]2=[O:25]>CC(C)=O>[C:23]12([CH2:33][S:34]([OH:37])(=[O:35])=[O:36])[C:30]([CH3:32])([CH3:31])[CH:27]([CH2:28][CH2:29]1)[CH2:26][C:24]2=[O:25].[CH3:1][O:2][C:3](=[O:21])[CH:4]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:20])[N:5]1[CH2:10][CH2:9][C:8]2[S:11][CH:12]=[CH:13][C:7]=2[CH2:6]1

参加物

4

反応物 2

HCID 2806(RS)-ClopidogrelHCID 1226536210-Camphorsulfonic acid monohydrate

生成物 1

HCID 156143992-chlorophenyl(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetic acid methyl ester (-)-camphorsulfonic acid salt収率 88%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒2 回

実験手順

32 g (0.0994 mol) of (2-chlorophenyl)(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetic acid methyl ester is dissolved in 150 ml of acetone and to the solution 9.95 g (0.0397 mol) of laevorotatory 10-camphorsulfonic acid monohydrate is added. The homogenous reaction mixture is allowed to stay at room temperature. After 48 hours a few crystals appear. The mixture is concentrated by evaporation to 50 ml and allowed to stay at room temperature for 24 hours. The resulting crystals are filtered off, washed with acetone and dried. The crystals thus obtained are dissolved again in a very small amount (50 ml) of hot acetone and after cooling the crystals are filtered off, washed with acetone and dried. Thus the title compound is obtained. Yield: 88%. Mp.: 165° C. [α]20D=+24° (c=1.68 g/100 ml; methanol).

後処理

  1. additionis added
  2. customto stay at room temperature
  3. concentrationThe mixture is concentrated by evaporation to 50 ml
  4. waitto stay at room temperature for 24 hours
  5. filtrationThe resulting crystals are filtered off
  6. washwashed with acetone
  7. customdried
  8. customThe crystals thus obtained
  9. temperatureafter cooling the crystals
  10. filtrationare filtered off
  11. washwashed with acetone
  12. customdried

出典と根拠

ORDレコード
ord-e717ee0e6ce142ffa3a09e6b570b643e
出典データセット
uspto-grants-2001_04
特許番号
US06215005B1

関連ノート

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