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Claims for Patent: 9,085,553

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Claims for Patent: 9,085,553

Title:LFA-1 inhibitor and methods of preparation and polymorph thereof
Abstract: Methods of preparation and purification of a compound of Formula I, intermediates thereof, a polymorph thereof, and related compounds are disclosed. Formulations and uses thereof in the treatment of LFA-1 mediated diseases are also disclosed. ##STR00001##
Inventor(s): Zeller; James Robert (Scottsdale, AZ), Venkatraman; Sripathy (Slingerlands, NY), Brot; Elisabeth C. A. (Albany, NY), Iyer; Subashree (Guilderland, NY), Hall; Michael (Albany, NY)
Assignee: SARCODE BIOSCIENCE, INC. (Brisbane, CA)
Application Number:13/950,807
Patent Claims: 1. A method of synthesizing a compound of Formula I: ##STR00029## or a salt thereof, comprising the steps: a) performing hydrolysis of Formula AA with a base under biphasic conditions: ##STR00030## wherein R is a carbon-containing moiety or a silyl-containing moiety; and b) isolating said compound of Formula I or a salt thereof.

2. The method of claim 1, wherein the biphasic conditions include aqueous acetone.

3. The method of claim 2, wherein the aqueous acetone is about 30% aqueous acetone.

4. The method of claim 2, wherein the aqueous acetone is present in an amount ranging from about 1:1 to about 5:1 by weight with respect to Formula AA.

5. The method of claim 1, wherein the base is sodium hydroxide.

6. The method of claim 5, wherein the sodium hydroxide is added in an amount ranging from about 1.0 to about 1.5 equivalents.

7. The method of claim 6, wherein the sodium hydroxide is added in an amount of about 1.2 equivalents.

8. The method of claim 1, further comprising a phase transfer catalyst.

9. The method of claim 8, wherein said phase transfer catalyst is a quaternary ammonium salt.

10. The method of claim 9, wherein said quaternary ammonium salt is tetrabutylammonium hydroxide.

11. The method of claim 8, wherein said phase transfer catalyst is present in an amount ranging from about 0.01 equivalents to about 0.5 equivalents.

12. The method of claim 1, wherein R is a substituted or unsubstituted group selected from lower alkyl, lower alkenyl, lower alkynyl, cyclo(lower)alkyl, cyclo(lower)alkenyl, aryl, aralkyl, heterocyclyl, and heteroaryl groups.

13. The method of claim 1, wherein Formula AA is: ##STR00031##

14. The method of claim 1, further comprising purifying said compound of Formula I by recrystallization.

15. The method of claim 14, wherein said recrystallization is performed with aqueous acetone.

16. A composition comprising a compound of Formula I: ##STR00032## wherein said compound is synthesized by a process comprising the following steps: a) performing hydrolysis of Formula AA with a base under biphasic conditions: ##STR00033## wherein R is a carbon-containing moiety or a silyl-containing moiety; and b) isolating said compound of Formula I or a salt thereof, and further wherein said compound has an optical purity of >98%.
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