Hydrochloric Acid → Prostaglandin B2

HRID 1576361Notes

Reaction equation

HRID 1576361 reaction equation
[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]1O.[OH-].[K+].Cl>C(O)C>[CH3:1][CH2:2][CH2:3][CH2:4][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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 5280360Prostaglandin E2

Product 1

HCID 5280881Prostaglandin B2

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
10 °C

Procedure

A solution of racemic PGE2 (200 mg.) in 100 ml. of 50% aqueous ethanol containing 10 grams of potassium hydroxide is kept at 25° C. for 10 hours under nitrogen. 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 PGB2.

Workup

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

Sources & evidence

ORD record
ord-13060ca778b54a268e15439819a0470b
Source dataset
uspto-grants-1976_09
Patent number
US03980691

Reaction notes

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