Methods for synthesis of acyloxyalkyl compounds
View Patent ↗Disclosed herein are methods for synthesizing 1-(acyloxy)-alkyl prodrug derivatives of drugs through oxidation of 1-acyl-alkyl derivatives of drugs under anhydrous reaction conditions. The methods typically proceed stereospecifically, in high yield, do not require the use of activated intermediates and/or toxic compounds and are readily amenable to scale-up.
1. A compound according to formula (I):
wherein:
R 1 and R 3 are each independently selected from hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, and tert-butyl;
R 2 is hydrogen;
n is 1;
X is oxygen; and
Y is —NRR′, wherein HNRR′ is selected from gabapentin, pregabalin, and baclofen.
2. The compound according to claim 1 , wherein HNRR′ is gabapentin.
3. The compound according to claim 2 , wherein R 1 is isopropyl and R 3 is methyl.
4. The compound according to claim 1 , wherein HNRR′ is pregabalin.
5. The compound according to claim 4 , wherein R 1 is isopropyl and R 3 is methyl.
6. The compound according to claim 1 , wherein HNRR′ is baclofen.
7. The compound according to claim 6 , wherein R 1 is isopropyl and R 3 is isopropyl.