HCID 15224614, compound → HCID 15224615, compound

HRID 373598Notes

Reaction equation

HRID 373598 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 (2.60 M, 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-9f5133a92f1a447fa64739cb95d39d9a
Source dataset
uspto-grants-1992_11
Patent number
US05164415

Reaction notes

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