Hydrochloric Acid → 9-Oxo-15S-hydroxy-5Z,8(12),13E,17Z-prostatetraenoic acid

HRID 1076079Notes

Reaction equation

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

Participants

Conditions

Temperature: 10 °C

Procedure

A solution of racemic PGE3 (200 mg.) in 100 ml. of 50% aqueous ethanol containing 10 grams of potassium hydroxide is kept at 25° C. for 10 hours under notrogen. Then, the solution is cooled to 10° C. and neutralized by addition of 3 normal hydrochloric acid at 10° C. The resulting solution is extracted repeatedly with ethyl acetate, and the combined ethyl acetate extracts are washed with water and then with saturated aqueous sodium chloride solution, dried, and evaporated to give racemic PGB3.

Workup

extractionThe resulting solution is extracted repeatedly with ethyl acetate
washthe combined ethyl acetate extracts are washed with water
dry with materialwith saturated aqueous sodium chloride solution, dried
customevaporated

Sources & evidence

ORD record: ord-03f36092e84743d7891e50c35a0a07d0
Source dataset: uspto-grants-1976_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03954851

Reaction notes

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