Triphenylphosphine → N-(2,2-Diphenylethyl)-N-(2-chloro-3-trifluoromethylbenzyl)-2,2-dimethyl-3-(3-aminopropoxy)phenylpropionic Acid

Participants

Role	Name	HCID	Charge
Reactant	Triphenylphosphine	HCID 11776	—
Reactant	Diisopropyl azodicarboxylate	HCID 5363146	—
Reactant	3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propan-1-ol	HCID 57757117	—
Reactant	Methyl 2,2-dimethyl-3-(3-hydroxyphenyl)propionate	HCID 67520417	—
Solvent	Water	HCID 962	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	N-(2,2-Diphenylethyl)-N-(2-chloro-3-trifluoromethylbenzyl)-2,2-dimethyl-3-(3-aminopropoxy)phenylpropionic Acid	HCID 68864466	50%

Reaction Steps

A solution of methyl 2,2-dimethyl-3-(3-hydroxyphenyl)propionate (135 mg, 0.65 mmol) and N-(2,2-diphenylethyl)-N-(2-chloro-3-trifluoromethylbenzyl)-3-hydroxypropylamine (290 mg, 0.65 mmol) in THF (8 mL) was treated with Ph3P (170 mg, 0.65 mmol), diisopropylazodicarboxylate (135 mg, 0.65 mmol), and stirred for 16 h. The reaction was diluted with H2O and extracted with Et2O. The extracts were washed with H2O, dried, and concentrated. Purification via silica gel column chromatography eluted with 30% EtOAc:hexane yielded the titled compound (200 mg, 50%). MS (ESI) 639 (M+H+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07560586B2
Source dataset	uspto-grants-2009_07
ORD ID	ord-958175d07f5c4b8c9fbd1e1ffcded43c
Source note	uspto-grants-2009_07