Acetic Acid → HCID 178484167, compound

Participants

Reaction Conditions

Reaction Steps

N-(2-amino-5-(oxetan-3-yl)phenyl)-3-(3-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(methyl)amino)cyclobutyl)propanamide (0.446 g, 0.752 mmol) was taken up in acetic acid (7.7 mL, 140 mmol) and heated at 65° C. for 3.5 h; HPLC/LC MS indicated complete conversion. At 3.75 h the acetic acid was removed by distillation with minimal warming to afford an orange oil, which was taken up in CH2Cl2 (45 mL) and washed with saturated aqueous NaHCO3 (2×30 mL). The aqueous layer was treated with NaCl until saturated and extracted with CH2Cl2 (2×20 mL). The combined organic layers were dried (Na2SO4) and concentrated in vacuo to afford a light orange oil. Purification by column chromatography (2×8 cm silica; 0-5% 7 N methanolic NH3/CH2Cl2) afforded the title compound (0.28 g, 65%) as a light orange foam: MS (ESI+) for C30H38N8O4 m/z 575.3 (M+H)+; MS (ESI−) for C30H38N8O4 m/z 573.3 (M−H)−; HPLC purity >95% (ret. time 2.142 min).

Provenance & Evidence