Chloroform → HCID 67726520, compound

2,5-Anhydro-1-deoxy-1- (adenin-9-yl) -D-allitol (916 mg) was subjected to azeotropic dehydration with anhydrous pyridine and then suspended in 15 ml of anhydrous pyridine. To the suspension was added 2.75 g of benzoyl chloride dropwise under ice-cooling. After the mixture was reacted at room temperature for 2 hours, it was poured into a mixture of 114 g of ice, 9 g of sodium hydrogen carbonate and 100 ml of chloroform and extracted with chloroform. The chloroform layer was concentrated and ethanol/pyridine was added to the residue. Then, 13 ml of 2N-sodium hydroxide solution and 13 ml of ethanol were added under water-cooling and the reaction was carried out at room temperature for 30 minutes. This reaction mixture was neutralized by adding about 13 ml of 2N-hydrochloric acid under cooling and concentrated under reduced pressure. The residue was washed with ether and the aqueous layer was concentrated under reduced pressure. The residue was purified by reversed phase column chromatography (methanol/water) to provide 1.28 g of the desirable compound. m.p. 85°-90° C.

1. temperaturecooling
2. customAfter the mixture was reacted at room temperature for 2 hours
3. extractionextracted with chloroform
4. concentrationThe chloroform layer was concentrated
5. additionethanol/pyridine was added to the residue
6. additionThen, 13 ml of 2N-sodium hydroxide solution and 13 ml of ethanol were added under water-
7. temperaturecooling
8. additionby adding about 13 ml of 2N-hydrochloric acid
9. temperatureunder cooling
10. concentrationconcentrated under reduced pressure
11. washThe residue was washed with ether
12. concentrationthe aqueous layer was concentrated under reduced pressure
13. customThe residue was purified by reversed phase column chromatography (methanol/water)

ORD record

ord-275f9cdf56324ffb98a9b51fdd304719

Source dataset

uspto-grants-1997_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05703224