Acetic Acid → PGF1alpha

HRID 1283483

Reaction equation

HRID 1283483 reaction equation
[BH4-].[Na+].[CH3:3][CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]([OH:27])/[CH:9]=[CH:10]/[C@@H:11]1[C@@H:16]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[C:14](=[O:15])[CH2:13][C@H:12]1[OH:26].CC(C)=O.C(O)(=O)C>CO>[CH3:3][CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]([OH:27])/[CH:9]=[CH:10]/[C@@H:11]1[C@@H:16]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[C@@H:14]([OH:15])[CH2:13][C@H:12]1[OH:26]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 4311764Sodium borohydrideHCID 5280723Alprostadil

Product 1

HCID 5280939PGF1alpha

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

Refer to Chart E wherein E is --CH=CH--, R2 and R4 are methyl, V is ---(CH2)5 --, W is 1-pentyl, and ~ is either alpha or beta. A solution of sodium borohydride (0.6 g.) in 10 ml. of methanol at 0° C. is added to a solution of PGE1, methyl ester, 15-methyl ether (Example 5, 1.5 g.) in 60 ml. of methanol and the mixture is stirred at 0° C. for 30 minutes. Acetone (10 ml.) is added and the solution is made slightly acid with dilute acetic acid in methanol. The mixture is concentrated by evaporation under reduced pressure and the residue is taken up in dichloromethane. The resulting solution is washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue is chromatographed over silica gel wet-packed in 8% methanol in dichlormethane ad rinsed with 300 ml. of dichloromethane, eluting with 2-10% methanol-dichloromethane. Those fractions shown by TLC to contain PGF1α , methyl ester, 15-methyl ether free of starting material and impurities are combined and concentrated to yield the Formula -VI PGF1α -type title compound. Likewise, those fractions shown by TLC to contain PGF1β, methyl ester, 15-methyl ether are combined and concentrated to yield the Formula-VI PGF1β -type title compound.

Workup

  1. concentrationThe mixture is concentrated by evaporation under reduced pressure
  2. washThe resulting solution is washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue is chromatographed over silica gel wet-packed in 8% methanol in dichlormethane ad
  6. washrinsed with 300 ml
  7. washof dichloromethane, eluting with 2-10% methanol-dichloromethane
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f895040f04e54d15bc0ce025db2c38af
Source dataset
uspto-grants-1976_08
Patent number
US03975404

Linked notes

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