4-Methylmorpholine → N-Cbz-5-hydroxy-L-norvaline methyl ester

Participants

Role	Name	HCID	Charge
Reactant	4-Methylmorpholine	HCID 7972	—
Reactant	Isobutyl chloroformate	HCID 62365	—
Reactant	(4S)-4-{[(benzyloxy)carbonyl]amino}-5-methoxy-5-oxopentanoic acid	HCID 2733408	—
Reactant	Sodium borohydride	HCID 4311764	—
Solvent	Methanol	HCID 887	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	N-Cbz-5-hydroxy-L-norvaline methyl ester	HCID 10588891	105%

Reaction Conditions

Temperature	-15 °C

Reaction Steps

To a cold (−15° C.) solution of Cbz-Glu-OMe (1.5 g) in THF (70 mL) was added N-methylmorpholine (0.616 mL) followed by isobutyl chloroformate (0.731 mL) dropwise. After 30 min stirring at −15° C., NaBH4 (576 mg) was added, followed MeOH dropwise. The reaction mixture was stirred at −10° C. for 15 min and quenched by the addition of 1M KHSO4 solution. The mixture was extracted with EA. The org. phase was washed with water, dried (Na2SO4) and evaporated off to give the crude product as a colourless oil (1.5 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08058263B2
Source dataset	uspto-grants-2011_11
ORD ID	ord-4f1ce3f10b7442eba7e321d9768f01b5
Source note	uspto-grants-2011_11