Triethylamine → methyl 2-[(2S)-2-{[(tert-butoxy)carbonyl]amino}-4-methylpentanamido]acetate

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-	HCID 83170	—
Reactant	Glycine methyl ester hydrochloride	HCID 122755	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	methyl 2-[(2S)-2-{[(tert-butoxy)carbonyl]amino}-4-methylpentanamido]acetate	HCID 6560406	—

Reaction Steps

In one aspect, substrates A and B were prepared as follows. To a solution of (S)-2-((tert-butoxycarbonyl)amino)-4-methylpentanoic acid (1w) in THF was added methyl 2-aminoacetate hydrochloride (2w), Et3N and HATU. The mixture was stirred at room temperature for 16 h. The reaction was filtered through Celite. The reaction filtrate was diluted with 100 mL of water and stirred for 15 min. The suspension was filtered off, rinsed with water and dried to afford (S)-methyl 2-(2-((tert-butoxycarbonyl)amino)-4-methylpentanamido)acetate (3w).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09447030B2
Source dataset	uspto-grants-2016_09
ORD ID	ord-4e40168ee3ac466fa1c67cd11595fa0a
Source note	uspto-grants-2016_09