Triethylamine → N-[N-(benzyloxycarbonyl)-N-methylvalyl]-L-aspartic acid di-tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	1-Hydroxybenzotriazole hydrate	HCID 2796029	—
Reactant	N-Methyl-N-[(phenylmethoxy)carbonyl]-L-valine	HCID 7016371	—
Reactant	L-Aspartic acid, bis(1,1-dimethylethyl) ester, hydrochloride	HCID 13768146	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	N-[N-(benzyloxycarbonyl)-N-methylvalyl]-L-aspartic acid di-tert-butyl ester	HCID 86714692	98%

Reaction Steps

To N-benzyloxycarbonyl-N-methyl-L-valine (0.50 g, 1.9 mmol), L-aspartic acid di-tert-butyl ester hydrochloride (0.53 g, 1.9 mmol), WSC hydrochloride (0.43 g, 2.3 mmol), and 1-hydroxybenzotriazole monohydrate (0.35 g, 2.3 mmol) were added tetrahydrofuran (10 ml) and triethylamine (0.39 mL, 2.8 mmol), and the mixture was stirred at room temperature for 5 hours. The reaction mixture was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20) to give the title compound (0.91 g, 1.8 mmol, 98%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09346821B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-1bef1f4f027c4f7fac8c0efe7fef9521
Source note	uspto-grants-2016_05