Diisopropylethylamine → 2-{3-[(1R,2R)-1-(2-Chlorobenzyl)-2-ethoxycarbonyl-2-hydroxy-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-4-(2-chloro-phenyl)-2-hydroxy-butyric acid ethyl ester	HCID 71073615	—
Solvent	Dichloromethane	HCID 6344	—
Product	2-{3-[(1R,2R)-1-(2-Chlorobenzyl)-2-ethoxycarbonyl-2-hydroxy-ethylcarbamoyl]-propyl}-benzoic Acid	HCID 71073721	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-4-(2-chloro-phenyl)-2-hydroxy-butyric acid ethyl ester (69.9 mg, 240 μmol, 1.0 eq.) was added and the mixture was stirred. The reaction was quenched after 1 hour by adding saturated NH4Cl and the product was extracted with DCM, dried and evaporated. The product was purified using preparative HPLC to yield the title compound (30 mg, 100% purity). MS m/z [M+H]+ calc'd for C23H26ClNO6, 448.14. found 448.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08686184B2
Source dataset	uspto-grants-2014_04
ORD ID	ord-336b4b4e026144c3ac6eaf25a68a632c
Source note	uspto-grants-2014_04