Triethylamine → methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanoate

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	1,4-Dioxane	HCID 31275	—
Reactant	4,4,5,5-Tetramethyl[1,3,2]dioxaborolane	HCID 2734768	—
Reactant	N-Boc-4-iodophenylalanine methylester	HCID 10319078	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanoate	HCID 10949509	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

PdCl2(dppf) (127 mg), triethylamine (2.14 ml), 4,4,5,5-tetramethyl-1,3,2-dioxaborolan (1.13 ml) and 1,4-dioxane (21 ml) were added to methyl (2S)-2-[(t-butoxycarbonyl)amino]-3-(4-iodophenyl)propionate (1.8 g) and stirred at 100° C. for 14 hours. The reaction solution was diluted with ethyl acetate, washed with water and dried over magnesium sulfate to remove the solvent. The residue was purified with a silica gel chromatography (hexane-ethyl acetate) to obtain the title compound (1.05 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07884204B2
Source dataset	uspto-grants-2011_02
ORD ID	ord-630641e897694613a39edb3139fe4c3b
Source note	uspto-grants-2011_02