4-Methylmorpholine → tert-Butyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamate

Participants

Role	Name	HCID	Charge
Reactant	4-Methylmorpholine	HCID 7972	—
Reactant	1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide	HCID 15908	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	N-(tert-butoxycarbonyl)glycine	HCID 78288	—
Reactant	Methanamine, N-methoxy-, hydrochloride (1:1)	HCID 81138	—
Solvent	Dichloromethane	HCID 6344	—
Product	tert-Butyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamate	HCID 4428209	71%

Reaction Steps

To a 2-(tert-butoxycarbonylamino)acetic acid (800 mg, 4.57 mmol), N,O-dimethylhydroxylamine hydrochloride (535 mg, 5.48 mmol), EDCI (1.05 g, 5.48 mmol), HOBt (740 mg, 5.48 mmol) in DCM (25 mL) was added NMM (2.77 g, 27.42 mmol) at rt. The reaction mixture was stirred overnight. After the reaction was completed, DCM was evaporated in vacuo. The residue was dissolved in MeOH, filtered through a syringe filter, and then purified by reverse-phase prep HPLC to provide the desired product (705 mg, 71%) as white solid

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07875647B2
Source dataset	uspto-grants-2011_01
ORD ID	ord-02f77e9a8e5c4c268fbfa94eb9ad0b5a
Source note	uspto-grants-2011_01