Reaktion #53998

Reaktionsgleichung

3-hydroxypropanoate

tert-butyl (5S,12S)-12-[(R)-[(3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(2,4-dioxo -3,4-dihydro-1(2H)-pyrimidinyl)tetrahydro-2-furanyl](hydroxy)methyl]-5-isobutyl-3,6-dioxo-1-phenyl-2-oxa-4,7,11-triazatridecan-13-oate

benzyl (1S)-1-methyl-2-oxo-2-[(3-oxopropyl)amino]ethylcarbamate

sodium triacetoxyborohydride

tetrahydrofuran

→

tert-butyl (5S,12S)-12-[(R)-[(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](hydroxy)methyl]-5-methyl-3,6-dioxo-1-phenyl-2-oxa-4,7,11-triazatridecan-13-oate

Ausbeute 39.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe product was purified by chromatography (flash column, silica gel, 5% methanol in methylene chloride)

Vorschrift

By using an analogous procedure to that described for Example 1, a solution of tert-(4-methoxybenzyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)-tetrahydro-2-furanyl]-3-hydroxypropanoate (80 mg, 0.111 mmol, obtained from Reference Example 6), benzyl (1S)-1-methyl-2-oxo-2-[(3-oxopropyl)amino]ethylcarbamate (39 mg, 0.139 mmol, obtained from Reference Example 20), acetic acid (1 drop), and sodium triacetoxyborohydride (47 mg, 0.222 mmol) in anhydrous tetrahydrofuran (4 ml) was stirred at room temperature under nitrogen for 3 hours. The product was purified by chromatography (flash column, silica gel, 5% methanol in methylene chloride) to provide tert-butyl (5S,12S)-12-[(R)-[(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](hydroxy)methyl]-5-methyl-3,6-dioxo-1-phenyl-2-oxa-4,7,11-triazatridecan-13-oate (43 mg, 39%) as a white amorphous solid.

Quelle