P,P-Diphenylphosphinic azide → (4S,5S)-4-(3,5-difluorobenzyl)-5-((2R,4S)-1-benzhydryl-4-hydroxypyrrolidin-2-yl)oxazolidin-2-one

Participants

Role	Name	HCID	Charge
Reactant	P,P-Diphenylphosphinic azide	HCID 199401	—
Reactant	tert-Butyl 3-((4S,5S)-4-(3,5-difluorobenzyl)-2-oxooxazolidin-5-yl)morpholine-4-carboxylate	HCID 67315602	—
Reactant	(2R,4R)-tert-butyl 2-((1S,2S)-2-(3,5-difluorobenzyl)-3-((S)-4-benzyl-2-oxooxazolidin-3-yl)-1-hydroxy-3-oxopropyl)-4-(allyloxy)pyrrolidine-1-carboxylate	HCID 67316359	—
Reactant	(2S,3S)-2-(3,5-difluorobenzyl)-3-((2R,4R)-4-(allyloxy)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-3-hydroxypropanoic acid	HCID 67316915	—
Solvent	Toluene	HCID 1140	—
Solvent	Triethylamine	HCID 8471	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	(4S,5S)-4-(3,5-difluorobenzyl)-5-((2R,4S)-1-benzhydryl-4-hydroxypyrrolidin-2-yl)oxazolidin-2-one	HCID 58608198	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

Step L (5): tert-Butyl 3-((4S,5S)-4-(3,5-difluorobenzyl)-2-oxooxazolidin-5-yl)morpholine-4-carboxylate. To a solution of (2S,3S)-2-(3,5-difluorobenzyl)-3-(4-(tert-butoxycarbonyl)morpholin-3-yl)-3-hydroxypropanoic acid (step L (6), 1.6 g, 4 mmol) in toluene (100 mL) was added diphenylphosphoryl azide (1.65 g, 6 mmol) and triethyl amine (1.01 g, 10 mmoL). This reaction mixture was stirred at 80° C. for 4 h. Ethyl acetate (500 mL) was added. The mixture was washed with sodium carbonate solution, H2O, dried over Na2SO4 and concentrated. The crude mixture was purified by silica gel Flash Chromatography (0% to 20% to 30% to 50% to 70% EtOAc/Hexane step gradient) to give 800 mg of the title compound: MS (ESI) (M−H)− 397.12.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07388007B2
Source dataset	uspto-grants-2008_06
ORD ID	ord-acb09f24b3e3472b9184ed889e1d556b
Source note	uspto-grants-2008_06