Thionyl Chloride → HCID 86588179, compound

Temperature

20 °C

Thionyl chloride (4.3 ml) was added to a stirred solution of (3aS,4S,6R,6aR)-6-(6-chloro-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (10.0 g), in chloroform (100 ml). The mixture was heated at reflux temperature under nitrogen for 60 min. After cooling to 20° C. the solvent was removed in vacuo and the residue azeotroped with toluene (2×50 ml). A suspension of the residue in chloroform (50 ml) was added dropwise at an equal rate with a solution of 1-amino-2-propanol (2.3 ml) and diisopropylethylamine (5.1 ml) in chloroform (50 ml) over 10 min to chloroform (50 ml) at 0° C. The mixture was stirred at 20° C. for 18 hours. Phosphate buffer (pH 6.5, 100 ml) was added and the phases separated. The aqueous phase was extracted with chloroform (50 ml). The combined chloroform layers were dried with sodium sulphate and the solvent removed in vacuo to give the title compound as a white foam (6.63 g).

1. temperatureThe mixture was heated
2. temperatureat reflux temperature under nitrogen for 60 min
3. customwas removed in vacuo
4. customthe residue azeotroped with toluene (2×50 ml)
5. additionA suspension of the residue in chloroform (50 ml)
6. additionwas added dropwise at an equal rate with a solution of 1-amino-2-propanol (2.3 ml) and diisopropylethylamine (5.1 ml) in chloroform (50 ml) over 10 min to chloroform (50 ml) at 0° C
7. additionPhosphate buffer (pH 6.5, 100 ml) was added
8. customthe phases separated
9. extractionThe aqueous phase was extracted with chloroform (50 ml)
10. dry with materialThe combined chloroform layers were dried with sodium sulphate
11. customthe solvent removed in vacuo

ORD record

ord-9ec1866c13904ec1baf76093c74aec88

Source dataset

uspto-grants-2004_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06677316B2