Reacción #54020

Ecuación de reacción

5-isobutyl-3,6-dioxo-1-phenyl-2-oxa-4,7,11-triazatridecan-13-oate

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

trifluoroacetic acid

→

(5S,12S)-12-[(R)-[(3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)-3,4-dihydroxy-tetrahydro-2-furanyl](hydroxy)methyl]-5-isobutyl-3,6-dioxo-1-phenyl-2-oxa-4,7,11-triazatridecan-13-oic acid

Rendimiento 15.4%

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe volatiles were removed
2. 2
   Otrothe residue was azeotroped with toluene
3. 3
   OtroThe resulting residue was purified by preparative HPLC (20×250 mm YMC-ODS column eluted with 10-70% acetonitrile in water containing 0.02% trifluoroacetic acid over 49 minutes)

Procedimiento

By using an analogous procedure to that described for Example 47, 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 (123 mg, 0.136 mmol, obtained from Example 6), trifluoroacetic acid (5 ml) and water (6 drops) were stirred for 10 hours at room temperature. The volatiles were removed and the residue was azeotroped with toluene. The resulting residue was purified by preparative HPLC (20×250 mm YMC-ODS column eluted with 10-70% acetonitrile in water containing 0.02% trifluoroacetic acid over 49 minutes) to provide (5S,12S)-12-[(R)-[(3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)-3,4-dihydroxy-tetrahydro-2-furanyl](hydroxy)methyl]-5-isobutyl-3,6-dioxo-1-phenyl-2-oxa-4,7,11-triazatridecan-13-oic acid (13 mg, 15%) as a white solid.

Fuente