Acetic Acid → methyl fluoro[(1S,5S)-5-hydroxycyclopent-2-en-1-yl]acetate

HRID 402925Notes

Reaction equation

HRID 402925 reaction equation
[Cl-].[Na+].C(O)(=O)C.[F:7][C:8]([C@H:17]1[C@H:21]([OH:22])[CH2:20][CH:19]=[CH:18]1)(C(OC)=O)[C:9]([O:11][CH3:12])=[O:10].FC([C@@H]1[C@@H](O)CC=C1)(C(OC)=O)C(OC)=O.FC([C@H]1[C@H](O)CC=C1)C(OC)=O>CS(C)=O>[F:7][CH:8]([C@@H:17]1[C@@H:21]([OH:22])[CH2:20][CH:19]=[CH:18]1)[C:9]([O:11][CH3:12])=[O:10]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 5234Sodium ChlorideHCID 44539493dimethyl fluoro[(1R,5R)-5-hydroxycyclopent-2-en-1-yl]propanedioateHCID 44539494dimethyl fluoro[(1S,5S)-5-hydroxycyclopent-2-en-1-yl]propanedioateHCID 59434306Methyl fluoro[(1R,5R)-5-hydroxycyclopent-2-en-1-yl]acetate

Product 1

HCID 58193987methyl fluoro[(1S,5S)-5-hydroxycyclopent-2-en-1-yl]acetate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
115 °C

Procedure

1 mL of dimethyl sulfoxide, 0.073 g (1.25 mmol) of sodium chloride, and 0.061 g (1.00 mmol) of acetic acid were added to 0.232 g (1.00 mmol) of a mixture of the compound of the formula 8a and the compound of the formula 8b, and the mixture was heated and stirred at 110 to 120° C. for 5 hours. After allowing it to cool, analysis was carried out using a high-performance liquid chromatography, and it was found that 0.146 g (the value quantitatively determined by high performance liquid chromatography) of a mixture of the compound of the formula 9a and the compound of the formula 9b was obtained.

Workup

  1. temperatureto cool

Sources & evidence

ORD record
ord-cd21a82cfaa54b119cecfa15f0621d20
Source dataset
uspto-grants-2014_06
Patent number
US08742161B2

Reaction notes

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