Phenylacetyl chloride → N-{[9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl]methyl}-2-phenylacetamide

A stirred solution of (2R,3R,4S,5R)-2-{2-(aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol (example 1) (220 mg, 0.45 mmol) in dichloromethane (10 ml) was treated with triethylamine (0.38 ml, 2.70 mmol) and phenylacetylchloride (280 mg, 1.80 mmol) at 0° C. and the resultant mixture stirred for 15 min. The mixture was then stirred at room temperature for 72 hr. The solvent was removed under reduced pressure and methanol (20 ml), saturated with ammonia gas, added. The resultant mixture was stirred at room temperature for 2 hr, treated with 2 molar aqueous sodium hydroxide (10 ml) and then left standing at room temperature for 24 hr. The methanol was removed under reduced pressure and the aqueous layer extracted with dichloromethane (×3). The combined organic layers were washed with water (×2), dried with anhydrous magnesium sulfate, filtered and the solvent removed under reduced pressure. The residue was dissolved in 1,4-dioxan (6 ml), 0.88 aqueous ammonia solution (8 ml) added and the mixture stirred at room temperature for 10 days. The 1,4-dioxan was removed under reduced pressure and the aqueous layer extracted with dichloromethane (×3).

1. customThe solvent was removed under reduced pressure and methanol (20 ml), saturated with ammonia gas
2. additionadded
3. stirringThe resultant mixture was stirred at room temperature for 2 hr
4. additiontreated with 2 molar aqueous sodium hydroxide (10 ml)
5. waitleft
6. waitstanding at room temperature for 24 hr
7. customThe methanol was removed under reduced pressure
8. extractionthe aqueous layer extracted with dichloromethane (×3)
9. washThe combined organic layers were washed with water (×2)
10. dry with materialdried with anhydrous magnesium sulfate
11. filtrationfiltered
12. customthe solvent removed under reduced pressure
13. dissolutionThe residue was dissolved in 1,4-dioxan (6 ml)
14. addition0.88 aqueous ammonia solution (8 ml) added
15. stirringthe mixture stirred at room temperature for 10 days
16. customThe 1,4-dioxan was removed under reduced pressure
17. extractionthe aqueous layer extracted with dichloromethane (×3)

ORD 기록

ord-3c4111335b6543b980e2ae5dd3f2cc60

출처 데이터셋

uspto-grants-2001_12

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06326359B1