Trifluoroacetic acid water → (R)-3-(2-(((R)-1-(3-(4-chlorophenyl)isoxazol-5-yl)ethyl)amino)pyrimidin-4-yl)-4-((R)-1-hydroxyethyl)oxazolidin-2-one

Participants

Role	Name	HCID	Charge
Reactant	Trifluoroacetic acid water	HCID 22392675	—
Reactant	(4R)-3-[2-[[1-[3-(4-Chlorophenyl)-5-isoxazolyl]ethyl]amino]-4-pyrimidinyl]-4-[(1R)-1-(1,1-dimethylethoxy)ethyl]-2-oxazolidinone	HCID 90415932	—
Product	(R)-3-(2-(((R)-1-(3-(4-chlorophenyl)isoxazol-5-yl)ethyl)amino)pyrimidin-4-yl)-4-((R)-1-hydroxyethyl)oxazolidin-2-one	HCID 90414298	—
Product	(R)-3-(2-(((S)-1-(3-(4-chlorophenyl)isoxazol-5-yl)ethyl)amino)pyrimidin-4-yl)-4-((R)-1-hydroxyethyl)oxazolidin-2-one	HCID 90414332	—

Reaction Steps

(4R)-4-((R)-1-(tert-butoxy)ethyl)-3-(2-((1-(3-(4-chlorophenyl)isoxazol-5-yl)ethyl)amino)pyrimidin-4-yl)oxazolidin-2-one (3.50 g, 2.88 mmol) was treated with 90% TFA/water for 2 hours. Concentrated in vacuo and neutralized by passing through a column of MP-carbonate resin (6.0 g, 0.55 mmol/g eluting with MeOH/DCM/MeOH afforded the diastereomeric mixture. Chiral SFC chromatography on an OJ-H column (75 g/min, 120 bar, 21×250 mm) eluting 30% IPA+10 mM NH4OH/CO2 (v/v) to give (R)-3-(2-(((S)-1-(3-(4-chlorophenyl)isoxazol-5-yl)ethyl)amino)pyrimidin-4-yl)-4-((R)-1-hydroxyethyl)oxazolidin-2-one and (R)-3-(2-(((R)-1-(3-(4-chlorophenyl)isoxazol-5-yl)ethyl)amino)pyrimidin-4-yl)-4-((R)-1-hydroxyethyl)oxazolidin-2-one.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09434719B2
Source dataset	uspto-grants-2016_09
ORD ID	ord-9f3b855d85b94319b687da9d8dfb12ed
Source note	uspto-grants-2016_09