Process for and intermediates in the preparation of canfosfamide and its salts
A process for and intermediates in the preparation of canfosfamide and its salts. Some of the intermediates have anticancer activity.
1. A compound of the formula
where R 1 is an amine-protecting group, or its salt.
2. The compound of claim 1 where R 1 is a catalytically removable amine-protecting group.
3. The compound of claim 2 where R 1 is (optionally substituted benzyl)oxycarbonyl or (optionally substituted allyl)oxycarbonyl.
4. The compound of claim 3 where R 1 is benzyloxycarbonyl.
5. A method of preparing canfosfamide or its salt, comprising deprotecting a compound of formula I:
where R 1 is an amine protecting group, or its salt, optionally followed by forming a salt of confosfamide;
wherein the compound of formula I is prepared by a method comprising oxidizing a compound of claim 1 .
6. The method of claim 5 , where the deprotecting comprises catalytic reduction or isomerization.
7. The method of claim 6 , where the deprotecting comprises reaction with hydrogen in the presence of palladium on carbon.
8. The method of claim 5 , where the hydrochloride salt of canfosfamide is formed by the addition of hydrogen chloride gas.
9. The method of claim 5 where R 1 is (optionally substituted benzyl)oxycarbonyl or (optionally substituted allyl)oxycarbonyl.
10. The method of claim 5 where the oxidizing comprises reaction with a persulfate.