N6-Benzoyl-2'-fluoro-2'-deoxyarabinoadenosine synthesis
- Product Name:N6-Benzoyl-2'-fluoro-2'-deoxyarabinoadenosine
- CAS Number:144924-99-2
- Molecular formula:C17H16FN5O4
- Molecular Weight:373.34
135473-17-5
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Yield:144924-99-2 86.7%
Reaction Conditions:
with water;sodium hydroxide in pyridine;methanol at -5 - 0; for 0.5 h;
Steps:
a.22 Preparation of compound 32-5:
To a solution of 32-4 (see WO 2012159047) (252.0 g, 433.30 mmol) was dissolved in pyridine (2.5 L), the mixture solution was cooled to 0°C. Then a solution of 2N NaOH (MeOH:H2O=4:1) (800 mL, 1.6 mol) was added to the mixture at 0°C, the resulting solution was stirred at 0°C to -5°C for 30 min. LCMS showed that 32-4 was consumed. The mixture was adjusted to pH = 7 with sat.NH4Cl. Extract with EA(2.5 L*3), washed by brine. The mixture was concentrated under vacuum. The product was purified by silica gel column (PE:EA(2:1)) to give 32-5 (140.0g, 374.3 mmol, 86.7% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 11.24 (s, 1H), 8.78 (s, 1H), 8.61 (d, J = 2.0 Hz, 1H), 8.09 - 8.03 (m, 2H), 7.69 - 7.63 (m, 1H), 7.59 - 7.54 (m, 2H), 6.59 (dd, J = 13.5, 4.7 Hz, 1H), 6.02 (d, J = 5.0 Hz, 1H), 5.32 (dt, J = 52.6, 4.3 Hz, 1H), 5.14 (t, J = 5.7 Hz, 1H), 4.51 (dq, J = 19.0, 5.0 Hz, 1H), 3.91 (q, J = 4.9 Hz, 1H), 3.77 - 3.64 (m, 2H). ESI-LCMS: m/z 374 [M+H]+
References:
WO2021/119325,2021,A1 Location in patent:Paragraph 0060; 0381
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