Kilogram-scale synthesis of the CXCR4 antagonist GSK812397

Organic Process Research and Development

Volumn 13, Issue 4, 2009, Pages 781-785

  Boggs, Sharon ^a   Elitzin, Vassil I ^a   Gudmundsson, Kristjan ^a   Martin, Michael T ^a   Sharp, Matthew J ^a  

^a GLAXOSMITHKLINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 68349146267     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op9000675     Document Type: Article

References (17)

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3. For a related recent example described in this journal, please see: Crawford, J. B.; Chen, G.; Gauthier, D.; Wilson, T.; Carpenter, B.; Baird, I. R.; McEachern, E.; Kaller, A.; Harwig, C.; Atsma, B.; Skerlj, R.; Bridger, G. J. Org. Process Res. Dev. 2008, 12, 823.
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5. Over 33 million people were living with HIV as of 2007 according to UNAIDS, www.unaids.org.
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8. The high pH needed to extract 9 from water leads to competitive disproportionation to the corresponding alcohol and carboxylic acid Via the Cannizarro reaction. We have more recently found that phosphate buffer considerably reduces the rate of disproportionation and aids in extracting the product into an organic phase.
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13. Beschke, H. Aldrichim. Acta 1978, 11, 13
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15. Kilogram quantities of ketone 3 were purchased from Astatech, Inc., Bristol, PA, U.S.A.
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17. The free base of 12 was found to be unstable upon storage.