(S)-prop-1-en-2-yl 5,5-dimethyl-1-(N-methyl-N-(2-trimethylsilylethoxycarbonyl)amino)hexan-2-ylcarbamate → methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-5,5-dimethyl-1-(N-methyl-N-(2-trimethylsilylethoxycarbonyl)amino)hexan-2-ylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate

Participants

Role	Name	HCID	Charge
Reactant	(S)-prop-1-en-2-yl 5,5-dimethyl-1-(N-methyl-N-(2-trimethylsilylethoxycarbonyl)amino)hexan-2-ylcarbamate	HCID 59201306	—
Reactant	Carbamic acid,N-[2-[(R)-(3-chlorophenyl)(3R)-3-piperidinylmethoxy]ethyl]-,methyl ester	HCID 59598478	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-5,5-dimethyl-1-(N-methyl-N-(2-trimethylsilylethoxycarbonyl)amino)hexan-2-ylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate	HCID 68709121	—

Reaction Conditions

Temperature	50 °C

Reaction Steps

The resulting (S)-prop-1-en-2-yl 5,5-dimethyl-1-(N-methyl-N-(2-trimethylsilylethoxycarbonyl)amino)hexan-2-ylcarbamate was dissolved in THF (5 mL) and methyl 2-((R)-(3-chlorophenyl)((R)-piperidin-3-yl)methoxy)ethylcarbamate (40 mg, 0.1227 mmol, 1.1 equiv) added and the mixture heated to 50° C. overnight. After completion of the reaction, the solution was washed with 0.5 M HCl, brine, then dried over Na2SO4, filtered, and evaporated to afford crude methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-5,5-dimethyl-1-(N-methyl-N-(2-trimethylsilylethoxycarbonyl)amino)hexan-2-ylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate which was taken directly to the next step.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08487108B2
Source dataset	uspto-grants-2013_07
ORD ID	ord-2933a49e90114b7e86ecccb74188a313
Source note	uspto-grants-2013_07