Water → (2R)-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenylacetic acid

HRID 369907Notes

Reaction equation

[F:1][B-](F)(F)F.N#[O+].C([C@H]1[O:16][C:15](=O)[C@@:14]([C@@H:24]2[CH2:28][CH2:27][C:26](=NO)[CH2:25]2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:13]1)(C)(C)C.[OH2:31].C(OCC)(=O)C.N1C=CC=CC=1.[FH:44]>ClCCl>[F:44][C:26]1([F:1])[CH2:27][CH2:28][C@@H:24]([C@@:14]([OH:13])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15]([OH:16])=[O:31])[CH2:25]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 20 mg of nitrosonium tetrafluoroborate in 0.5 ml of 70% hydrogen fluoride-pyridine, a solution of 34 mg of (2R,5R)-2-(t-butyl)-5-((1R)-3-hydroxyiminocyclopentyl)-5-phenyl-1,3-dioxolan-4-one in 0.5 ml of dichloromethane was added under cooling with ice, followed by stirring for 10 minutes at 0° C. and for 5 hours at room temperature. Water was added to the reaction mixture under cooling with ice, and extraction was carried out with ethyl acetate. After sequential washing with a saturated aqueous solution of sodium hydrogencarbonate and brine, the organic layer was dried over anhydrous magnesium sulfate. Distilling the solvent off under reduced pressure gave 35 mg of the title compound.

Workup

temperatureunder cooling with ice
temperatureunder cooling with ice, and extraction
washAfter sequential washing with a saturated aqueous solution of sodium hydrogencarbonate and brine
dry with materialthe organic layer was dried over anhydrous magnesium sulfate
distillationDistilling the solvent off under reduced pressure

Sources & evidence

ORD record: ord-a5627e87915e4aac8f46ff7e9149549d
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06140333

Reaction notes

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