Trifluoroacetic acid → 2,2-dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4'-(pyrrolidin-2-yl)-[1,1'-biphenyl]-4-yl)propan-2-yl)acetamide

Participants

Role	Name	HCID	Charge
Reactant	Trifluoroacetic acid	HCID 6422	—
Reactant	tert-butyl 2-(4'-((1R,2S)-2-(2,2-dichloroacetamido)-3-fluoro-1-hydroxypropyl)-[1,1'-biphenyl]-4-yl)pyrrolidine-1-carboxylate	HCID 89519230	—
Solvent	Dichloromethane	HCID 6344	—
Product	2,2-dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4'-(pyrrolidin-2-yl)-[1,1'-biphenyl]-4-yl)propan-2-yl)acetamide	HCID 89515184	84.6%

Reaction Steps

To a solution of the product of step 1 (210 mg, 0.4 mmol) in DCM (3 mL) is added TFA (1 mL). The mixture is stirred for 1 hour. The reaction is then diluted with DCM, washed with sat.NaHCO3 (aq.) and evaporated to give the title compound (144 mg). 1H-NMR (400 MHz, DMSO) δ(ppm) 1.5-1.65 (1H), 1.7-1.9 (2H), 2.1-2.25 (1H), 2.8-3.0 (1H), 3.0-3.2 (1H), 4.05-4.15 (1H), 4.15-4.35 (1.5H), 4.35-4.45 (0.5H), 4.5-4.6 (0.5H), 4.65-4.75 (0.5H), 4.8-4.9 (1H), 5.9-6.0 (1H), 6.5 (1H), 7.4-7.5 (4H), 7.5-7.65 (4H), 8.6 (1H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09145355B2
Source dataset	uspto-grants-2015_09
ORD ID	ord-c6bc5b5d7a784f2c9578c79887d3bbe1
Source note	uspto-grants-2015_09