A fluorous-tagged, acid-labile protecting group for the synthesis of carboxamides and sulfonamides

Journal of Combinatorial Chemistry

Volumn 6, Issue 4, 2004, Pages 611-622

  Villard, Anne Laure ^a   Warrington, Brian H ^a   Ladlow, Mark ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; FLUORINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PROTECTIVE AGENT; SILICA GEL; SULFONAMIDE;

ACIDITY; ARTICLE; COLUMN CHROMATOGRAPHY; COMBINATORIAL CHEMISTRY; DRUG SYNTHESIS; ORGANIC CHEMISTRY; PURIFICATION; QUANTUM YIELD; REACTION ANALYSIS; SOLID PHASE EXTRACTION;

EID: 4143081635     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc0499338     Document Type: Article

References (27)

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26. 13 (R1 = R2 = Me). HPLC (method 2, 254 nm): tR = 8.56 min (100%). 1H NMR (400 MHz, CDCl3): <5H 1.73 (3H, s), 1.74 (3H, s), 2.11 (2H, m), 2.32 (2H, m), 2.37 (3H, s), 2.87 (2H, m), 3.07 (IH, m), 3.44 (IH, m), 3.84 (3H, s), 4.03 (2H, t, 7H,F = 6.0), 4.33 (IH, d, J = 15.0), 4.44 (IH, d, J = 15.0), 6.45 (2H, m), 7.11 (2H, d, J = 8.0), 7.21 (2H, d, 7 = 8.0), 7.28 (IH, d, 7 = 8.8), 7.44 (4H, m). 13C NMR (125 MHz, CDCl3): (5C 20.6 (1C), 21.0 (1C), 25.6 (1C), 27.2 (1C), 28.0 (1C, t, JC,F = 22.3), 34.5 (1C), 45.0 (1C, brs), 47.5 (1C, brs), 55.3 (1C), 66.4 (1C), 88.1 (1C), 98.8 (1C), 104.6 (1 C), 107.0-120.7 (m, C8Fn), 117.3 (1C), 126.8 (2C), 127.0 (2C), 129.0 (2C), 129.4 (2C), 131.2 (1C), 136.9 (1C), 137.7 (1C), 138.0 (1C), 139.2 (1C), 159.0 (1C), 159.6 (1C). LC/ MS (ESI): îR = 6.10 min (m/z 976.5,978.5 [M + HCOQ-]). 11 (R1 = R2 = Me): HPLC (method 2, 254 nm): iR = 8.00 min (100%). 1H NMR (400 MHz, CDCl3): ÔH 1 -27 (6H, d, J = 7.0), 2.11 (2H, m), 2.32 (2H, m), 2.37 (3H, s), 2.85 (2H, m), 2.95 (IH, m), 3.41 (2H, m), 3.83 (3H, s), 4.03 (2H, t, /H,F = 6.0), 4.44 (2H, s), 6.45 (2H, m), 7.16 (2H, d, 7 = 8.0), 7.21 (2H, d, / = 8.0), 7.32 (IH, d, / = 8.8), 7.44 (4H, m). 13C NMR (125 MHz, CDCl3): ôc 16.6 (1C), 20.6 (1C), 21.0 (1C), 28.0 (1C, t, 7C,F = 22.1), 35.4 (2C), 45.6 (1C), 49.7 (1C), 53.9 (1C), 55.3 (1C), 66.4 (1C), 98.8 (1C), 104.7 (1 C), 107.0-120.7 (m, C8F17), 117.4 (1C), 126.8 (2C), 127.0 (2C), 129.2 (2C), 129.4 (2C), 131.7 (1C), 136.9 (1C), 137.6 (1C), 137.9 (1C), 139.3 (1C), 158.6 (1C), 159.7 (1C). LC/ MS (ESI): iR = 6.08 min (m/z 958.3 [M + HCOQ-]). 13 (R1 = H, R2 = Me): HPLC (method 2, 254 nm): ?R = 7.92 (44%) and 8.36 min (56%). 1H NMR (400 MHz, CDCl3): OH 1-47 (1.32H, d, 7 = 7.0), 1.79 (1.68H, d, 7 = 7.0), 2.11 (2H, m), 2.32 (2H, m), 2.38 (3H, s), 2.85 (2H, m), 3.21 (IH, m), 3.41 (IH, m), 3.82 (3H, m), 4.03 (2H, m), 4.17 (IH, m), 4.47 (2H, m), 6.45 (2H, m), 7.13 (2H, m), 7.23 (3H, m), 7.45 (4H, m). 13C NMR (125 MHz, CDCl3): ôc 19.4 and 20.2 (1C), 20.6 (1C), 21.0 (1C), 28.0 (1C, t, 7C,F = 22.2), 34.8 and 35.1 (1C), 45.3 and 46.1 (1C), 48.4 and 49.1 (1C), 55.2 and 55.3 (1C), 66.3 and 66.4 (1C), 69.4 and 72.4 (1C), 98.9 and 99.0 (1C), 104.5 and 104.6 (1C), 107.0-120.7 (m, C8F17), 117.1 and 117.3 (1C), 126.7 and 126.8 (2C), 126.9 and 127.0 (2C), 129.0 and 129.1 (2C), 129.4 and 129.5 (2C), 131.2 and 131.8 (1C), 136.9 and 137.0 (1C), 137.6 and 137.7 (1C), 137.9 and 138.0 (1C), 139.2 and 139.4 (1C), 158.8 and 158.9 (1C), 159.7 and 159.9 (1C). LC/MS (ESI): îR = 5.88 (44%) and 6.03 (56%) min (m/z 962.2, 964.1 [M + HCOO-]). 11 (R1 = H, R2 = Me): HPLC (method 2, 254 nm): /R = 7.76 min (100%). 1H NMR (400 MHz, CDCl3): ÔH 1.25 (3H, t, J = 7.5), 2.11 (2H, m), 2.32 (2H, m), 2.35 (3H, s), 2.84 (4H, m), 3.42 (2H, m), 3.83 (3H, s), 4.04 (2H, t, 7H, F = 6.0), 4.42 (2H, s), 6.46 (2H, m), 7.18 (2H, d, 7 = 8.0), 7.22 (2H, d, J = 8.0), 7.31 (IH, d, J = 8.8), 7.46 (4H, m). 13C NMR (125 MHz, CDCl3): ôc 8.1 (1C), 20.6 (1C), 21.0 (1C), 28.0 (1C, t, 7C,F = 22.2), 35.2 (1C), 45.3 (1C), 47.0 (1C), 55.3 (1C), 66.4 (1C), 98.9 (1C), 104.7 (1C), 107.0-120.7 (m, C8F17), 117.2 (1C), 126.8 (2C), 127.0 (2C), 129.2 (2C), 129.5 (2C), 131.7 (1C), 137.0 (1C), 137.5 (1C), 137.9 (1C), 139.3 (1C), 1158.6 (1C), 159.8 (1C). LC/MS (ESI): tR = 5.79 min (m/z 944.7 [M + HCOO-]).
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