Triethylamine → (1R)-1-{[2(S)-(hex-5-enyl-methyl-carbamoyl)-4(R)-hydroxy-pyrrolidine-N-carbonyl]amino}-2(R)-vinyl-cyclopropanecarboxylic acid ethyl ester

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	(2S,4R)-N-(hex-5-enyl)-4-hydroxy-N-methylpyrrolidine-2-carboxamide	HCID 57816715	—
Reactant	1-((1R,2S)-1-(ethoxycarbonyl)-2-vinylcyclopropyl-carbamoyl)-3-methyl-1H-imidazol-3-ium iodide	HCID 86633206	—
Solvent	Dichloromethane	HCID 6344	—
Product	(1R)-1-{[2(S)-(hex-5-enyl-methyl-carbamoyl)-4(R)-hydroxy-pyrrolidine-N-carbonyl]amino}-2(R)-vinyl-cyclopropanecarboxylic acid ethyl ester	HCID 66650543	70%

Reaction Steps

Triethylamine (1.3 mL, 3 eq.) was added at room temperature under nitrogen to a mixture of compound 34 (0.7 g, 1 eq.) and compound 49 (1.2 g, 1 eq.) in DCM (15 mL). The reaction mixture was stirred overnight at room temperature and then quenched with 1M aqueous hydrochloric acid. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by chromatography on silica gel to yield compound 50 as a white solid in 70% yield.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08003659B2
Source dataset	uspto-grants-2011_08
ORD ID	ord-1d98916a4f124a0db5ccd2917722d979
Source note	uspto-grants-2011_08