4-Methylmorpholine → (S)-N-methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide

Participants

Role	Name	HCID	Charge
Reactant	4-Methylmorpholine	HCID 7972	—
Reactant	Methanamine, N-methoxy-, hydrochloride (1:1)	HCID 81138	—
Reactant	L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-	HCID 83170	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	1-Hydroxybenzotriazole hydrate	HCID 2796029	—
Solvent	Dimethylformamide	HCID 6228	—
Product	(S)-N-methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide	HCID 11119284	87.7%

Reaction Steps

A mixture of N-Boc-L-leucine (2.47 g), N,O-dimethylhydroxylamine hydrochloride (1.09 g), 1-hydroxybenzotriazole monohydrate (1.51 g), and N-methylmorpholine (1.21 mL) was dissolved in DMF (40 mL), 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.14 g) was added at 0° C. and the mixture was stirred at 0° C. for 2h, then at room temperature for 22 h. The reaction was quenched with water (100 mL) and the mixture was extracted with EtOAc (3×100 mL). The combined organic layers were washed with aqueous 10% HCl, saturated NaHCO3, and brine, then dried over anhydrous MgSO4, filtered, and evaporated to afford the product (2.57 g) as an oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06660268B1
Source dataset	uspto-grants-2003_12
ORD ID	ord-5a2f7bdc6da44fae9841726aae989bf5
Source note	uspto-grants-2003_12