2-Butenoic acid, 3-amino-, 1-methylethyl ester → Isradipine

HRID 2054706

反応式

HRID 2054706 の反応式
[CH3:1][O:2][C:3](=[O:18])[C:4]([C:15](=O)[CH3:16])=[CH:5][C:6]1[C:11]2=[N:12][O:13][N:14]=[C:10]2[CH:9]=[CH:8][CH:7]=1.[CH:19]([O:22][C:23](=[O:28])/[CH:24]=[C:25](\[NH2:27])/[CH3:26])([CH3:21])[CH3:20]>C(O)C>[CH3:16][C:15]1[NH:27][C:25]([CH3:26])=[C:24]([C:23]([O:22][CH:19]([CH3:21])[CH3:20])=[O:28])[CH:5]([C:6]2[C:11]3=[N:12][O:13][N:14]=[C:10]3[CH:9]=[CH:8][CH:7]=2)[C:4]=1[C:3]([O:2][CH3:1])=[O:18]

参加物

4

反応物 2

HCID 111372742-Butenoic acid, 3-amino-, 1-methylethyl esterHCID 534332132-Acetyl-3-benzofurazan-4-yl-acrylic acid methyl ester

生成物 1

HCID 3784Isradipine

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
26.5 °C

実験手順

Dissolved the purified 2-acetyl-3-benzofurazan-4-yl-acrylic acid methyl ester obtained in example—3 (25 g, 0.10 mol) in absolute ethanol (375 ml) and added in to the solution isopropyl-β-aminocrotonate (13.15 ml, 0.09 mol). Stirred the reaction mixture under nitrogen atmosphere at 25-28° C. for 5 hr. Removed sample from the reaction mixture and analysed the sample by qualitative HPLC. Distilled ethanol from the reaction mixture under vacuum at 50° C. Dissolved the residue in ethyl acetate (235 ml) and washed twice with water (90 ml). Dried the organic layer over sodium sulphate and distillation under vacuum at 50° C. Dissolved the concentrate in ethanol (65 ml at 70° C. and slowly cooled to 5° C. to get the product crystallised. Filtered the product and washed with pre cooled ethanol (25 ml and dried at 70° C. under vacuum to obtain 30 g Isradipine (purity=99.4%, Impurity III=0.22%, and Impurity IV=0.11% by HPLC.

後処理

  1. customRemoved sample from the reaction mixture
  2. customat 50° C
  3. dissolutionDissolved the residue in ethyl acetate (235 ml)
  4. washwashed twice with water (90 ml)
  5. customDried the organic layer
  6. distillationover sodium sulphate and distillation under vacuum at 50° C
  7. dissolutionDissolved the
  8. concentrationconcentrate in ethanol (65 ml at 70° C.
  9. temperatureslowly cooled to 5° C.
  10. customto get the product
  11. customcrystallised
  12. filtrationFiltered the product
  13. washwashed with pre
  14. temperaturecooled ethanol (25 ml
  15. customdried at 70° C. under vacuum

出典と根拠

ORDレコード
ord-b9c0846b1ca341ee8bc07fbde28fd441
出典データセット
uspto-grants-2008_02
特許番号
US07329756B2

関連ノート

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