Alprostadil → Pga1

HRID 1579731Notes

Reaction equation

HRID 1579731 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][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:12](=[O:13])[CH2:11][C@H:10]1O>C(O)(=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][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:12](=[O:13])[CH:11]=[CH:10]1

Participants

3

Reactant 1

HCID 5280723Alprostadil

Product 1

HCID 5281912Pga1

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 170 mg. of trans-Δ2 -PGE1 (prepared as described in Example 2) in 15 ml. of 90% acetic acid was stirred for 17 hours at a temperature of 57° to 60°C. The reaction mixture was concentrated under reduced pressure and the residue dissolved in diethyl ether, washed with water, dried, and concentrated under reduced pressure. The residue was further purified by column chromatography using 20 g. of silica gel and a cyclohexaneethyl acetate mixture (4:1) as eluent. The fraction containing trans-Δ2 -PGA1 was collected and concentrated. The product thus obtained was recrystallised from a cyclohexane-ethyl acetate mixture to obtain pure trans-Δ2 -PGA1 : yield 102 mg. (63%), m.p. 68°C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue dissolved in diethyl ether
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was further purified by column chromatography
  7. additionThe fraction containing trans-Δ2 -PGA1
  8. customwas collected
  9. concentrationconcentrated
  10. customThe product thus obtained
  11. customwas recrystallised from a cyclohexane-ethyl acetate mixture

Sources & evidence

ORD record
ord-f6781af6d906491e959da7e678685b06
Source dataset
uspto-grants-1976_01
Patent number
US03931296

Reaction notes

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