Solution-phase parallel synthesis of a benzoxazinone library using complementary molecular reactivity and molecular recognition (CMR/R) purification technology

Tetrahedron

Volumn 54, Issue 16, 1998, Pages 4013-4031

  Parlow, John J ^a   Flynn, Daniel L ^a  

^a MONSANTO COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOXAZINONE DERIVATIVE;

CONFERENCE PAPER; DRUG STRUCTURE; DRUG SYNTHESIS; FILTRATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MEDICAL TECHNOLOGY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; PURIFICATION; ROBOTICS;

EID: 0032537038     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00132-X     Document Type: Conference Paper

References (21)

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16. 4. Parlow, J. J.; Naing, W.; South, M. S.; Flynn, D. L. Tetrahedron Lett. 1997, 38, 7959.
17. 5. The reaction block employed in our robotics synthesis laboratory is a modified version of a commercially-available apparatus from Bohdan, INC, Mundelein, Illinois. The 6X8 array block has 48 medium-fritted pyrex reaction chambers, each capable of handling up to 9 mL total volume. Each row of vessels can be independently manipulated to allow for open valve position rinsing/draining or closed valve position for incubations. The block is equipped with an inert atmosphere manifold and has a performing temperature range of -40C to 120C.
18. 6. Polymeric DMAP is commercially available from Aldrich Chemical Company, Milwaukee, Wisconsin.
19. 7. Column f was not treated with the 2N HCl so as not to deprotect the Boc groups from the compounds in that column.
20. 8. Rosowsky, A.; Wright, J. E. J. Org. Chem. 1983, 48, 1539.
21. 9. The carbobenzyloxy-L-valine anhydride 18a was prepared directly from the acid 21a and 1.5 equivalents of polymeric-EDC (Scheme 4). See reference 1g and also: Desai, M. C.; Stramiello S. L. M. Tetrahedron Lett. 1993, 34, 7685. (equation presented) Scheme 4. In situ preparation of anhydride from acid using P-EDC. Amberlyst A-15®, Reg. trademark of Rohm and Haas Co.