Triethylamine → (2S)-2-{[(S)-(4-bromophenyl)(thien-2-yl)methyl]oxy}-N-(cyanomethyl)-4-methylpentanamide

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Sodium Bicarbonate	HCID 516892	—
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	Aminoacetonitrile hydrochloride	HCID 11491918	—
Reactant	(2S)-2-{[(S)-(4-bromophenyl)(thien-2-yl)methyl]oxy}-4-methylpentanoic acid	HCID 69473998	—
Solvent	Dimethylformamide	HCID 6228	—
Product	(2S)-2-{[(S)-(4-bromophenyl)(thien-2-yl)methyl]oxy}-N-(cyanomethyl)-4-methylpentanamide	HCID 10342122	—

Reaction Steps

To a solution of (2S)-2-{[(S)-(4-bromophenyl)(thien-2-yl)methyl]oxy}-4-methylpentanoic acid from step 2, (273 mg, 0.71 mmol) in DMF (3.5 mL) was added aminoacetonitrile HCL salt (66 mg, 0.71 mmol), triethylamine (359 μL, 3.55 mmol) and HATU (270 mg, 0.71 mmol). The mixture was aged for 3 hours under a nitrogen atmosphere and was then poured into a saturated aqueous solution of NaHCO3. The resulting mixture was extracted 3 times with ethyl acetate. The organic extracts were washed with brine, dried and evaporated to a solid. The crude product was chromatographed on silica gel using 35% ethyl acetate in hexanes to afford the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07279478B2
Source dataset	uspto-grants-2007_10
ORD ID	ord-e05bd8d4e74543fcb9a0ecbf21daec60
Source note	uspto-grants-2007_10