Alprostadil → Pga1

HRID 26304

Reaction equation

HRID 26304 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.O>[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 21899381Acetic acid--water (1/1)Solvent

Procedure

A 125 mg (0.3 mmol) portion of the prostaglandin E1 analogue of Example 3 (14-Phenyl-11α,15R-dihydroxy-9-oxoprost-10,13E-dien-1-oic acid) was stirred into 10 ml of acetic acid-water (2:1) at 50° C. under an inert atmosphere. Progress of the reaction was followed by thin layer chromatography. After 48 hours, the reaction mixture was extracted with ether. Ether layers obtained were combined and washed to neutrality with brine. Removal of the solvent yielded a yellow oil. The oil was azeotroped with toluene and chromatographed on 70 g SG-60, and eluted with benzene-ethanol (19:1) to yield 102 mg of the PGA1 analogue.

Workup

  1. extractionthe reaction mixture was extracted with ether
  2. customEther layers obtained
  3. washwashed
  4. customRemoval of the solvent
  5. customyielded a yellow oil
  6. customThe oil was azeotroped with toluene
  7. customchromatographed on 70 g SG-60
  8. washeluted with benzene-ethanol (19:1)

Sources & evidence

ORD record
ord-2c28d4190b6e46498a16bbc8b4c01369
Source dataset
uspto-grants-1979_04
Patent number
US04149007

Linked notes

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