Triethylamine → (R,E)-ethyl 3-(benzyloxycarbonylamino)-3-(3-(4-(4-bromo-2,6-dimethylphenyl)but-2-enamido)phenyl)propanoate

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate	HCID 151348	—
Reactant	(R)-ethyl 3-(3-aminophenyl)-3-(benzyloxycarbonylamino)propanoate	HCID 57842606	—
Reactant	(E)-4-(4-bromo-2,6-dimethylphenyl)but-2-enoic acid	HCID 57842884	—
Solvent	Acetonitrile	HCID 6342	—
Product	(R,E)-ethyl 3-(benzyloxycarbonylamino)-3-(3-(4-(4-bromo-2,6-dimethylphenyl)but-2-enamido)phenyl)propanoate	HCID 57842858	54%

Reaction Conditions

Temperature	0 °C

Reaction Steps

BOP (1.3 g, 3.0 mmol) was added to a solution of 53C (675 mg, 2.5 mmol), 39C (1.0 g, 2.75 mmol) and triethylamine (5.0 mmol) in acetonitrile (25 mL) at 0° C. The mixture was stirred at 0° C. for 2 h and at ambient temperature for 15 h. The mixture was concentrated in vacuo and purified by flash chromatography (0% to 60% EtOAc in hexanes) to afford 53D (800 mg, 54%) as a white solid. MS (ESI) m/z 593.3/595.3 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07592331B2
Source dataset	uspto-grants-2009_09
ORD ID	ord-59229cda631c4d779039754adac8b4dd
Source note	uspto-grants-2009_09