HCID 15224614, compound → HCID 15224615, compound

HRID 2226233Notes

Reaction equation

HRID 2226233 reaction equation
[F:1][CH:2]([C:10](=[O:40])[CH2:11][C@H:12]1[C@@H:16]([O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[CH2:15][C@@H:14]([O:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][O:26]2)[C@@H:13]1[CH2:31][CH2:32][CH:33]([OH:39])[CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[F:1][CH:2]([C:10](=[O:40])[CH2:11][C@H:12]1[C@@H:16]([O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[CH2:15][C@@H:14]([O:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][O:26]2)[C@@H:13]1[CH2:31][CH2:32][C:33](=[O:39])[CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 2

HCID 15224614HCID 15224614, compoundHCID 131709961Jones' reagent

Product 1

HCID 15224615HCID 15224615, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of methyl 5(RS)-fluoro-6-oxo-7{(1R,2R,3R,5S)-2-[3(RS)-hydroxy-1-octyl]-3,5-bis-tetrahydropyranyloxy-cyclopentyl}-6-oxo-heptanoate (54) (0.30 g) in acetone was added Jones reagent (2.60M, 0.6 ml) and the resultant mixture was stirred at -30° C. for 1.5 hours. The reaction mixture was treated in the conventional manner and the obtained crude product was subjected to silica gel column chromatography to give the title compound (55) as a mixture of diastereomers.

Workup

  1. additionThe reaction mixture was treated in the conventional manner
  2. customthe obtained crude product

Sources & evidence

ORD record
ord-5e8f179915be444880522bdf172c73b7
Source dataset
uspto-grants-1994_09
Patent number
US05346921

Reaction notes

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