Potassium Hydroxide → Zolmitriptan-2-carboxylic Acid

HRID 229755ノート

反応式

HRID 229755 の反応式
[OH-].[K+].C([O:5][C:6]([C:8]1[NH:9][C:10]2[C:15]([C:16]=1[CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])=[CH:14][C:13]([CH2:22][C@H:23]1[CH2:27][O:26][C:25](=[O:28])[NH:24]1)=[CH:12][CH:11]=2)=[O:7])C>C(O)C>[CH3:21][N:19]([CH3:20])[CH2:18][CH2:17][C:16]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:22][C@H:23]3[CH2:27][O:26][C:25](=[O:28])[NH:24]3)[CH:14]=2)[NH:9][C:8]=1[C:6]([OH:7])=[O:5]

参加物

4

反応物 2

HCID 14797Potassium HydroxideHCID 10498674Zolmitriptan 2-carboxylic acid ethyl ester

生成物 1

HCID 10449364Zolmitriptan-2-carboxylic Acid収率 299.8%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
5 °C

実験手順

To a solution of 1.4 g (24.9 mmoles) of KOH in 30 ml of ethanol was added 2.8 g (7.8 mmoles) of (S)-3-(2-dimethylaminoethyl)-5-[2-oxo-1,3-oxazolidin-4-ylmethyl]-1H-indol-2-carboxylic acid ethyl ester. The resulting solution was heated at reflux temperature for one hour. It was cooled and the solvent evaporated to dryness. The residue was dissolved in 6 ml of water and washed three times with 10 ml of dichloromethane. The aqueous solution was cooled to 5° C., adjusted to pH 6 with glacial acetic acid, stirred for 30 minutes at that temperature and the water evaporated to dryness. The residue was redissolved in 30 ml of water and 5 g of ionic exchange resin (Dowex 50WX8-400) added. The mixture was left under stirring at room temperature for 24 hours. The resin was filtered and it was washed with water. For desorption the resin was suspended with 20 ml of a 10% aqueous solution of ammonia and stirred at room temperature for 5 hours. Once that time had elapsed it was filtered and washed with water. The water was evaporated to dryness under reduced pressure to give 7.75 g (94%) of the title acid as a yellow crystalline solid:

後処理

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux temperature for one hour
  3. temperatureIt was cooled
  4. customthe solvent evaporated to dryness
  5. dissolutionThe residue was dissolved in 6 ml of water
  6. washwashed three times with 10 ml of dichloromethane
  7. customthe water evaporated to dryness
  8. dissolutionThe residue was redissolved in 30 ml of water
  9. addition5 g of ionic exchange resin (Dowex 50WX8-400) added
  10. waitThe mixture was left
  11. stirringunder stirring at room temperature for 24 hours
  12. filtrationThe resin was filtered
  13. washit was washed with water
  14. stirringstirred at room temperature for 5 hours
  15. filtrationwas filtered
  16. washwashed with water
  17. customThe water was evaporated to dryness under reduced pressure

出典と根拠

ORDレコード
ord-9e3e9dee3ce84e46b14656a3cd2d99a8
出典データセット
uspto-grants-2009_07
特許番号
US07563904B2

反応ノート

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