Réaction #54005

Équation de réaction

tert-butyl (2S,3R)-3-[(3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(3-(4-methoxybenzyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)tetrahydro-2-furanyl]-2-[(11-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}undecanoyl)amino]-3-hydroxypropanoate

piperidine

→

tert-butyl (2S,3R)-2-[(11-aminoundecanoyl)amino]-3-[(3R,4R,5R)-3,4-bis{[tert-butyl (dimethyl)silyl]oxy}-5-(3-(4-methoxybenzyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)tetrahydro-2-furanyl]-3-hydroxypropanoate

Rendement 65.0%

Conditions de réaction

Traitement

1. 1
   AutreThe product was purified by chromatography (flash column, silica gel, 50-60% methanol in methylene chloride)

Mode opératoire

By using an analogous procedure to that described for Reference Example 32, tert-butyl (2S,3R)-3-[(3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(3-(4-methoxybenzyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)tetrahydro-2-furanyl]-2-[(11-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}undecanoyl)amino]-3-hydroxypropanoate (73 mg, 0.065 mmol, obtained from Example 22) was stirred with piperidine (1.5 ml) for 1 hour under nitrogen at room temperature. The product was purified by chromatography (flash column, silica gel, 50-60% methanol in methylene chloride) to provide tert-butyl (2S,3R)-2-[(11-aminoundecanoyl)amino]-3-[(3R,4R,5R)-3,4-bis{[tert-butyl (dimethyl)silyl]oxy}-5-(3-(4-methoxybenzyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)tetrahydro-2-furanyl]-3-hydroxypropanoate (38 mg, 65%) as a white solid.

Source