Dimethylformamide → methyl N-{[4-({[(benzyloxy)carbonyl]amino}methyl)cyclohexyl]carbonyl}-L-norleucinate

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Triethylamine	HCID 8471	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate	HCID 2733207	—
Reactant	Cbz-trans-4-(aminomethyl)cyclohexanecarboxylic acid	HCID 3723035	—
Solvent	Water	HCID 962	—
Product	methyl N-{[4-({[(benzyloxy)carbonyl]amino}methyl)cyclohexyl]carbonyl}-L-norleucinate	HCID 69803360	77%

Reaction Steps

To a stirring mixture of 4-({[(benzyloxy)carbonyl]amino}methyl)cyclohexanecarboxylic acid (750 mg, 2.57 mmol), TBTU (1.08 g, 3.34 mmol), and HOBT (55 mg, 0.03 mmol) in DMF (15 mL) was added the norleucine OMe HCl (411 mg, 2.83 mmol), followed by addition of triethylamine (898 μL, 6.43 mmol). The resulting mixture was then stirred at ambient temperature for 2 hours, diluted with water and the resulting precipitate was collected by filtration and dried in a vacuum oven to provide the titled compound (830 mg, 1.98 mmol, 77%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06972340B2
Source dataset	uspto-grants-2005_12
ORD ID	ord-d3e4ea6171f64419853ca8606e5dd651
Source note	uspto-grants-2005_12