Acetic Acid → ethyl (5S)-12-[(R)-[(2R, 3R,4 R,5R)-3,4-bis(acetyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2 h)-yl)tetrahydrofuran-2-yl](hydroxy)methyl]-3,6-dioxo-1-phenyl-5-[(1S)-1-(tetradecanoyloxy)ethyl]-2-oxa-4,7,11-triazatridecan-13-oate

Participants

Reaction Steps

By using an analogous procedure to that described for Example 56, a solution of (1S,2S)-2-1[(benzyloxy)carbonyl]amino}-1-methyl-3-oxo-3-[(3-oxopropyl)amino]propyl myristate (250 mg, 0.483 mmol, obtained from Reference Example 48) and the hydrogen chloride salt mixture of ethyl (2R,3R)-3-(acetyloxy)-2-dihydro-1(2H)-pyrimidinyl)tetrahydro-2-furanyl]propanoate and ethyl (2R,3R)-3-(acetyloxy)-2-{[(benzyloxy)carbonyl]amino}-3-[(2R,3R,4R,5S)-3,4-bis(acetyloxy)-5-(2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)tetrahydro-2-furanyl]propanoate (207 mg, 0.483 mmol, obtained from Reference Example 46), acetic acid (0.028 ml, 0.483 mmol) and sodium triacetoxyborohydride (205 mg, 0.97 mmol) in anhydrous tetrahydrofuran (4 ml) was stirred at room temperature under a nitrogen atmosphere for 16 hours. The product was chromatographed (flash column, silica gel, 75% ethyl acetate in hexane) to provide ethyl (5S)-12-[(R)-[(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2 h)-yl)tetrahydrofuran-2-yl](hydroxy)methyl]-3,6-dioxo-1-phenyl-5-[(1S)-1-(tetradecanoyloxy)ethyl]-2-oxa-4,7,11-triazatridecan-13-oate (100 mg, 22%) as a white amorphous solid.

Provenance & Evidence