US 7,321,064 B1
Preparation of amides of retinoic acid via mixed anhydride and mixed carbonate intermediates
John E. Cabaj, Sheboygan, Wis. (US); and Jeff J. Hutchison, Sheboygan, Wis. (US)
Assigned to Cedarburg Pharmaceuticals, Inc., Grafton, Wis. (US)
Filed on Mar. 08, 2007, as Appl. No. 11/715,571.
Int. Cl. C07C 231/00 (2006.01)
U.S. Cl. 564—133 19 Claims
 
1. A process for preparing an amide of retinoic acid, the process comprising:
(a) reacting a retinoic acid having the formula:

OG Complex Work Unit Drawing
or isomers thereof with a compound having a formula selected from:

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and

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wherein R is alkyl or aryl or alkoxy, and X is a halogen, to produce an intermediate having the formula:

OG Complex Work Unit Drawing
and
(b) reacting the intermediate with 4-aminophenol to produce an amide of retinoic acid having the formula:

OG Complex Work Unit Drawing
or isomers thereof.