Potassium Carbonate → (4S,5S)-4-(3,5-difluorobenzyl)-5-((2R,4S)-1-benzhydryl-4-hydroxypyrrolidin-2-yl)oxazolidin-2-one

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	Bromodiphenylmethane	HCID 236603	—
Reactant	(4S,5S)-4-(3,5-Difluorobenzyl)-5-((R)-4-benzhydrylmorpholin-3-yl)oxazolidin-2-one	HCID 67315700	—
Reactant	(2S,3S)-2-(3,5-difluorobenzyl)-3-((2R,4R)-4-(allyloxy)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-3-hydroxypropanoic acid	HCID 67316915	—
Reactant	(4S,5S)-4-(3,5-difluorobenzyl)-5-((R)-1-benzhydrylpiperidin-2-yl)oxazolidin-2-one	HCID 69195572	—
Solvent	Acetonitrile	HCID 6342	—
Product	(4S,5S)-4-(3,5-difluorobenzyl)-5-((2R,4S)-1-benzhydryl-4-hydroxypyrrolidin-2-yl)oxazolidin-2-one	HCID 58608198	29%

Reaction Conditions

Temperature	100 °C

Reaction Steps

Step L (7): (4S,5S)-4-(3,5-Difluorobenzyl)-5-((R)-4-benzhydrylmorpholin-3-yl)oxazolidin-2-one. To a solution of (4S,5S)-4-(3,5-difluorobenzyl)-5-(morpholin-3-yl)oxazolidin-2-one (step L (6), 180 mg, 0.6 mmol) in acetonitrile (5 mL) were added potassium carbonate (248 mg, 1.8 mmol) and bromodiphenylmethane (296 mg, 1.2 mmol). This mixture was stirred at 100° C. for 1.5 h. Solvent was removed and the crude mixture was purified by silica gel Flash Chromatography (0% to 20% to 40% to 65% EtOAc/Hexane step gradient) to give 85 mg of the title compound (29% yield):

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07388007B2
Source dataset	uspto-grants-2008_06
ORD ID	ord-b9c564c842224d0691e37a8553f9a9c6
Source note	uspto-grants-2008_06