Acetic Acid → HCID 44366862, Verbindung

A mixture of 16 (50 mg, 0.1 mmol), acetic acid (7 μL, 0.12 mmol), and 0.17 mL of 1M tetrabutylammonium fluoride in THF (0.17 mmol) was stirred in 10 mL tetrahydrofuran overnight. Water (2 mL) and 15 mL ethyl ether were added followed by stirring for 5 minutes. The organic phase was extracted with 2 mL water and then the combined aqueous solution was washed with 15 mL ethyl ether. The aqueous extract was concentrated in vacuo to 1 mL and then applied to a 4-mL Dowex 1×4 100-200 (-3OH) column to remove tetrabutylammonium salts by eluting with water followed by 20% aqueous methanol. The solvent was removed in vacuo and the product was recrystallized from ethanol/ethyl acetate to afford 19.5 mg (54%) of 17; mp. 187°-90° C. dec; FAB MS 267 (M+H)+ ; 1H NMR (DMSO-d6) δ 8.0 (s, 1, H-8), 6.68 (br, s, 2, NH2), 5.95 (m, 1, I'-H), 5.71 (brs, 2, NH2), 5.22 (m, 1, 5'-OH), 3.73 (m, 1, 5'-H), 3.57 (m, 2, 4'-H, 5'-H), 2.4 (m, 1, 2'-H), 2.32 (m, 1, 2'-H), 2.12 (m, 1, 3'-H), 1.98 (m, 1, 3'-H).

1. extractionThe organic phase was extracted with 2 mL water
2. washthe combined aqueous solution was washed with 15 mL ethyl ether
3. extractionThe aqueous extract
4. concentrationwas concentrated in vacuo to 1 mL
5. customto remove tetrabutylammonium salts
6. washby eluting with water
7. customThe solvent was removed in vacuo
8. customthe product was recrystallized from ethanol/ethyl acetate

ORD-Eintrag

ord-2b15bd030f194f75b6c9f4ca14224b7c

Quelldatensatz

uspto-grants-1995_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05478928