Dimethylformamide → tert-Butyl 3-methoxybenzyl((2R,3S)-3-(3-acetyl-5-(benzamido)benzamido)-4-(3,5-difluorophenyl)-2-hydroxybutyl)carbamate

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
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	5-Acetyl-N-methyl-N-propyl-isophthalamic acid	HCID 57529285	—
Reactant	tert-butyl 3-methoxybenzyl((2R,3S)-3-amino-4-(3,5-difluorophenyl)-2-hydroxybutyl)-carbamate	HCID 68827600	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	tert-Butyl 3-methoxybenzyl((2R,3S)-3-(3-acetyl-5-(benzamido)benzamido)-4-(3,5-difluorophenyl)-2-hydroxybutyl)carbamate	HCID 68827142	—

Reaction Steps

A mixture of 3-acetyl-5-(methyl(propyl)carbamoyl)-benzoic acid (from step 3, 0.386 mmol), HATU (176 mg, 0.464 mmol) and Hunig's base (200 mg, 0.3 mL, 1.545 mmol) in DMF (4.0 mL) was stirred for 10 min and then tert-butyl 3-methoxybenzyl((2R,3S)-3-amino-4-(3,5-difluorophenyl)-2-hydroxybutyl)-carbamate (168 mg, 0.386 mmol) was added. The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate and washed with H2O 3 times. The organic layer was dried over sodium sulfate and concentrated under vacuum. The crude product was purified by reverse phase prep HPLC to give the title compound (100 mg): HPLC retention time: 2.185 min (method A). MS (ESI) (M+H)+ 682.32.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07476764B2
Source dataset	uspto-grants-2009_01
ORD ID	ord-e987beea6f2b461588d83d52c8b396e9
Source note	uspto-grants-2009_01