Diisopropylethylamine → 2-Methoxycarbamoyl-piperazine-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	O-Methylhydroxylamine hydrochloride	HCID 521874	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	4-((Benzyloxy)carbonyl)-1-((tert-butoxy)carbonyl)piperazine-2-carboxylic acid	HCID 2756778	—
Solvent	Dichloromethane	HCID 6344	—
Product	2-Methoxycarbamoyl-piperazine-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester	HCID 87321032	—

Reaction Steps

To a solution of piperazine-1,2,4-tricarboxylic acid 4-benzyl ester 1-tert-butyl ester (0.364 g, 1 mmol) in dichloromethane (3 mL) was added O-Methyl Hydroxylamine HCl (95 mg, 1.13 mmol), EDC HCl (0.3 g, 1.57 mmol) and DIEA (0.28 g, 2.17 mmol). The resulting mixture was stirred at room temperature overnight and partitioned between dichloromethane and water. The combined organic extracts were washed with brine, dried, and evaporated. The residue was purified by flash column chromatography on silica gel, eluting with EtOAc/n-Hexane (30/70) to afford the title product.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08263781B2
Source dataset	uspto-grants-2012_09
ORD ID	ord-a47809f47f594252908baefb03d8ed93
Source note	uspto-grants-2012_09