Potassium Acetate → 8-Isoprostaglandin E2

HRID 1576898

反応式

HRID 1576898 の反応式
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:25])/[CH:7]=[CH:8]/[C@@H:9]1[C@@H:14]([CH2:15]/[CH:16]=[CH:17]\[CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:12](=[O:13])[CH2:11][C@H:10]1[OH:24].C([O-])(=O)C.[K+]>C(O)C>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:25])/[CH:7]=[CH:8]/[C@@H:9]1[C@H:14]([CH2:15]/[CH:16]=[CH:17]\[CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:12](=[O:13])[CH2:11][C@H:10]1[OH:24]

参加物

4

反応物 2

HCID 517044Potassium AcetateHCID 5280360Prostaglandin E2

生成物 1

HCID 52832138-Isoprostaglandin E2

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of 1.00 g. of racemic PGE2 and 5 g. of potassium acetate in 100 ml. of 95% ethanol is allowed to stand at room temperature under nitrogen for 6 days; then is concentrated by evaporation under reduced pressure to about one third volume. The concentrated mixture is diluted with 75 ml. of cold water and dilute hydrochloric acid is added until the mixture reaches pH 3. The acidified mixture is extracted twice with ethyl acetate, then is saturated with sodium chloride and extracted once more with ethyl acetate. The ethyl acetate extracts are combined, washed with saturated aqueous sodium chloride, dried over sodium sulfate, and evaporated under reduced pressure, then dried under a stream of nitrogen to remove acetic acid from the residue. Thin layer chromatographic analysis shows that the residue comprises a mixture of racemic PGE2 and racemic 8-iso PGE2. The residue is chromatographed on 200 g. of Silicar CC4, eluting with 500 ml. 40%, 500 ml. 50%, 250 ml. 60%, and 250 ml. 100% ethyl acetate in cyclohexane, collecting 50-ml. fractions. Fractions 23-25 are combined and evaporated to give racemic 8-iso-PGE2. Fractions 27-30 are combined to give racemic PGE2.

後処理

  1. concentrationthen is concentrated by evaporation under reduced pressure to about one third volume
  2. additionThe concentrated mixture is diluted with 75 ml
  3. additionof cold water and dilute hydrochloric acid is added until the mixture
  4. extractionThe acidified mixture is extracted twice with ethyl acetate
  5. extractionextracted once more with ethyl acetate
  6. washwashed with saturated aqueous sodium chloride
  7. dry with materialdried over sodium sulfate
  8. customevaporated under reduced pressure
  9. customdried under a stream of nitrogen
  10. customto remove acetic acid from the residue
  11. additiona mixture of racemic PGE2 and racemic 8-iso PGE2
  12. customThe residue is chromatographed on 200 g
  13. washof Silicar CC4, eluting with 500 ml
  14. custom100% ethyl acetate in cyclohexane, collecting 50-ml
  15. customevaporated

出典と根拠

ORDレコード
ord-f8871b68139d4bb0a064a6bf02600c8b
出典データセット
uspto-grants-1976_09
特許番号
US03983153

関連ノート

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