HCID 22813268, compound → HCID 22813302, compound

HRID 1732217Notes

Reaction equation

HRID 1732217 reaction equation
[O:1]1[C@H:12]2[CH2:13][C@@H:14]([CH3:26])[C@@H:15](/[CH:16]=[CH:17]/[C@@H:18]([OH:25])[C@H:19]([F:24])[CH2:20][CH2:21][CH2:22][CH3:23])[C@H:11]2[CH2:10][C@@H:2]1[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8]>C(OCC)(=O)C.[Pt]=O>[O:1]1[C@H:12]2[CH2:13][C@@H:14]([CH3:26])[C@H:15]([CH2:16][CH2:17][C@@H:18]([OH:25])[C@H:19]([F:24])[CH2:20][CH2:21][CH2:22][CH3:23])[C@H:11]2[CH2:10][C@@H:2]1[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8]

Participants

4

Reactant 1

HCID 22813268HCID 22813268, compound

Product 1

HCID 22813302HCID 22813302, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 275 mg of [6S,8R,9S,11R,12S,15R,16R]-6,9-epoxy-11-methyl-16-fluoro-15-hydroxyprost-(13E)-enoic acid in 20 ml of ethyl acetate was added 30 mg of platinum oxide. The mixture was sealed under a positive hydrogen atmosphere and vigorously stirred. After eight hours, the reaction mixture was filtered and the volatiles removed by rotary evaporation. The residual oily product was purified by chromatography over 50 g of Sephadex LH-20 using chloroform-hexane (65/35) to yield [6S,8R,9S,11R,12S,15R,16R]-6,9-epoxy-11-methyl-16-fluoro-15-hydroxyprostanoic acid.

Workup

  1. customThe mixture was sealed under a positive hydrogen atmosphere
  2. filtrationthe reaction mixture was filtered
  3. customthe volatiles removed by rotary evaporation
  4. customThe residual oily product was purified by chromatography over 50 g of Sephadex LH-20 using chloroform-hexane (65/35)

Sources & evidence

ORD record
ord-d2994f458e1642449f99846285c732c3
Source dataset
uspto-grants-1980_12
Patent number
US04237060

Reaction notes

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