Triethylamine → (3R,4S,5S,6S)-N-(1-Carbamoylethyl)-5-(5-isopropyl-2-methoxybenzylamino)-6-diphenylmethyl-1-azabicyclo[2.2.2]octane-3-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Sodium Bicarbonate	HCID 516892	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	L-Alaninamide--hydrogen bromide (1/1)	HCID 18632422	—
Reactant	(3R,4S,5S,6S)-5-(5-isopropyl-2-methoxybenzylamino)-6-diphenylmethyl-1-azabicyclo[2.2.2]octane-3-carboxylic acid dihydrochloride	HCID 70115624	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	(3R,4S,5S,6S)-N-(1-Carbamoylethyl)-5-(5-isopropyl-2-methoxybenzylamino)-6-diphenylmethyl-1-azabicyclo[2.2.2]octane-3-carboxamide	HCID 9894241	78%

Reaction Conditions

Temperature	0 °C

Reaction Steps

To a mixture of (3R,4S ,5S ,6S)-5-(5-isopropyl-2-methoxybenzylamino)-6-diphenylmethyl-1-azabicyclo[2.2.2]octane-3-carboxylic acid dihydrochloride (300 mg, 0.5 mmol), alaninamide hydrobromide (100 mg, 0.6 mmol) and triethylamine (70 mg, 0.7 mmol) in DMF (2 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (160 mg, 0.8 mmol) at 0° C. The mixture was stirred at 0° C. for 30 minutes, then at room temperature for 14 hours. Water and NaHCO3 were added and the mixture was extracted with CH2Cl2. The combined extracts were dried, concentrated and purified by a column chromatography on silica-gel (CH2Cl2 /methanol=10:1) to give a title compound (220 mg, 0.39 mmol, 77%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05569662
Source dataset	uspto-grants-1996_10
ORD ID	ord-a1110a829a7f4879b1176bed03dd5924
Source note	uspto-grants-1996_10