Hydrochloric Acid → Treprostinil

HRID 39617

反応式

HRID 39617 の反応式
[OH:1][C@H:2]1[C@H:18]([CH2:19][CH2:20][C@@H:21]([OH:27])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C@H:5]2[CH2:6][C:7]3[C:12]([CH2:13][C@H:4]2[CH2:3]1)=[C:11]([O:14][CH2:15][C:16]#N)[CH:10]=[CH:9][CH:8]=3.[OH-:28].[K+].Cl.C[OH:32]>>[CH3:26][CH2:25][CH2:24][CH2:23][CH2:22][C@H:21]([OH:27])[CH2:20][CH2:19][C@H:18]1[C@H:2]([OH:1])[CH2:3][C@H:4]2[C@@H:5]1[CH2:6][C:7]1[C:12]([CH2:13]2)=[C:11]([O:14][CH2:15][C:16]([OH:32])=[O:28])[CH:10]=[CH:9][CH:8]=1

参加物

5

反応物 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 11314741Descarboxymethyl Cyanomethyl Treprostinil

生成物 1

HCID 6918140Treprostinil収率 81%

反応条件

温度
10 °C

実験手順

2-((1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-((S)-3-hydroxyoctyl)-1H-cyclopent a[b]naphthalen-5-yloxy)acetonitrile (2 g, 0.005 mmol) in methanol (18 ml) was treated with 20% KOH (6 ml) and refluxed for 3 hr. The reaction was then cooled to 10° C. and 3N HCl was added slowly until pH=˜8. The solvent was removed in vacuo. Ethyl acetate and brine were added and then 3N HCl was added slowly until pH=2. The reaction mixture was extracted with ethyl acetate. The combined ethyl acetate extracts were dried over anhydrous magnesium sulfate. The solid was filtered off. The solvent was evaporated off under vacuum. The crude product was purified by crystallization from ethanol/H2O. The titled compound was obtained in a crystalline form. Yield: 81%.

後処理

  1. temperaturerefluxed for 3 hr
  2. customThe solvent was removed in vacuo
  3. additionEthyl acetate and brine were added
  4. addition3N HCl was added slowly until pH=2
  5. extractionThe reaction mixture was extracted with ethyl acetate
  6. dry with materialThe combined ethyl acetate extracts were dried over anhydrous magnesium sulfate
  7. filtrationThe solid was filtered off
  8. customThe solvent was evaporated off under vacuum
  9. customThe crude product was purified by crystallization from ethanol/H2O

出典と根拠

ORDレコード
ord-40e7ce238e8048ec9f2c34e20916919d
出典データセット
uspto-grants-2013_09
特許番号
US08524939B2

関連ノート

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