Diisopropylethylamine → 2-{3-[(1R,2R)-2-Ethoxycarbonyl-2-hydroxy-1-(2-trifluoromethyl-benzyl)-ethylcarbamoyl]-propyl}-benzoic acid

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	2-(3-Carboxypropyl)benzoic acid	HCID 12422083	—
Reactant	(2R,3R)-3-amino-2-hydroxy-4-(2-trifluoromethyl-phenyl)-butyric acid ethyl ester	HCID 71073550	—
Solvent	Dichloromethane	HCID 6344	—
Product	2-{3-[(1R,2R)-2-Ethoxycarbonyl-2-hydroxy-1-(2-trifluoromethyl-benzyl)-ethylcarbamoyl]-propyl}-benzoic acid	HCID 71073603	100%

Reaction Steps

2-(3-Carboxy-propyl)benzoic acid (50 mg, 240 μmol, 1.0 eq.) was combined with DIPEA (134 μL, 3.2 eq.) and HATU (91.3 mg, 240 μmol, 1.0 eq.) in DCM (5 mL). (2R,3R)-3-Amino-2-hydroxy-4-(2-trifluoromethyl-phenyl)-butyric acid ethyl ester (69.9 mg, 240 μmol, 1.0 eq.) was added and the resulting mixture was stirred for 1 hour. The reaction was quenched by adding saturated NH4Cl and the product was extracted with DCM, dried, evaporated, and purified by preparative HPLC to yield the title compound (40 mg, 100% purity). MS m/z [M+H]+ calc'd for C24H26F3NO6, 482.17. found 482.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08686184B2
Source dataset	uspto-grants-2014_04
ORD ID	ord-08f68ffe1fe44fc6b90bf08ebb78fe65
Source note	uspto-grants-2014_04