4-Methylmorpholine → N-(t-Butyloxy)-2(R)-[[4-methoxybenzenesulfonyl](3-picolyl)amino]-3-methylbutanamide

https://huagongshe.com/en/reaction/742021

Participants

Role	Name	HCID	Charge
Reactant	4-Methylmorpholine	HCID 7972	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	O-tert-butylhydroxylamine hydrochloride	HCID 2777906	—
Reactant	2(R)-[[4-methoxybenzenesulfonyl](3-picolyl)amino]-3-methyl-butanoic acid hydrochloride	HCID 70061703	—
Solvent	Water	HCID 962	—
Solvent	Dichloromethane	HCID 6344	—
Product	N-(t-Butyloxy)-2(R)-[[4-methoxybenzenesulfonyl](3-picolyl)amino]-3-methylbutanamide	HCID 10671218	—

Reaction Steps

2(R)-[[4-methoxybenzenesulfonyl](3-picolyl)amino]-3-methylbutanoic acid hydrochloride (5.0 g, 12.06 mmol), 1-hydroxybenzotriazole (1.63 g, 12.06 mmol), 4-methylmorpholine (6.6 mL, 60.31 mmol), and O-t-butylhydroxylamine hydrochloride (54.55 g, 36.19 mmol) are dissolved in methylene chloride (200 mL). N-[Dimethylaminopropyl]-N'-ethylcarbodiimide hydrochloride (3.01 g, 15.68 mmol) is added, and the reaction is stirred overnight. The reaction is then diluted with water and extracted with methylene chloride. The combined organic extracts are washed with brine, dried (Na2SO4), and the solvent is evaporated. The crude product is purified by silica gel chromatography (2% methanol/methylene chloride) to give N-(t-butyloxy)-2(R)-[[4-methoxybenzenesulfonyl]-(3-picolyl)amino]-3-methylbutanamide.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05552419
Source dataset	uspto-grants-1996_09
ORD ID	ord-89b984171886441980757aaf2b85ab7a
Source note	uspto-grants-1996_09