Novel quenchers for solution phase parallel synthesis

Tetrahedron Letters

Volumn 39, Issue 10, 1998, Pages 1121-1124

  Nikam, Sham S ^a   Kornberg, Brian E ^a   Ault Justus, Stephanie E ^a   Rafferty, Michael F ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMINO ACID DERIVATIVE; CHLORIDE; ISOCYANIC ACID DERIVATIVE; SULFONAMIDE;

ACYLATION; ARTICLE; CHEMICAL MODIFICATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

EID: 0032485516     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10781-X     Document Type: Article

References (9)

1. 1. Thompson, L.A., Ellman, J.A. Chem. Rev. 1996, 96, 555. Hermkens, P.H.H.; Ottenheijm, H.C.J.; Rees, D. Tetrahedron, 1996, 52, 4527.
2. 1. Thompson, L.A., Ellman, J.A. Chem. Rev. 1996, 96, 555. Hermkens, P.H.H.; Ottenheijm, H.C.J.; Rees, D. Tetrahedron, 1996, 52, 4527.
3. 2. Hodges, J. C.; Booth, R. J. J. Am. Chem. Soc. 1997, 119, 4882-4886. Kaldor, S.W.; Siegel, M.G.; Fritz, J.E.; Dressman, B.A.; Hahn, P.J. Tetrahedron Lett., 1996, 37, 7193; Keating, T. A.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 2574.
4. 2. Hodges, J. C.; Booth, R. J. J. Am. Chem. Soc. 1997, 119, 4882-4886. Kaldor, S.W.; Siegel, M.G.; Fritz, J.E.; Dressman, B.A.; Hahn, P.J. Tetrahedron Lett., 1996, 37, 7193; Keating, T. A.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 2574.
5. 2. Hodges, J. C.; Booth, R. J. J. Am. Chem. Soc. 1997, 119, 4882-4886. Kaldor, S.W.; Siegel, M.G.; Fritz, J.E.; Dressman, B.A.; Hahn, P.J. Tetrahedron Lett., 1996, 37, 7193; Keating, T. A.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 2574.
6. 3. Gayo, L.M.; Suto, M.J. Tetrahedron Lett., 1997, 38, 513.
7. 4. Cheng, S.; Comer, D.D.; Williams, J.P.; Myers, P.L.; Boger, D.L. J. Am. Chem. Soc. 1996,118, 2567.
8. 5. The ureas were synthesized by treating N-methylbenzylamine (0.302 g, 2.5 mmol) with isocyanate (3.5 mmol) in THF (5 mL) / triethylamine (0.695 g, 5 mmol) and quenching with K sarcosinate (0.19 g, 1.5 mmol) followed by aqueous quench.
9. 6. The amides and sulfonamides were synthesized by treating N-benzylmethylamine (0.302 g, 2.5 mmol) with an acid chloride or sulfonyl chloride (3.5 mmol) in DMF (2 mL) and triethylamine (0.695 g, 5 mmol). Reaction was quenched with K sarcosinate (0.127 g, 1 mmol) and water (6 mL). The product was isolated by filtration in the case of solids and extracted in ETOAc (10 mL) in the case of oils. EtOAc extract was pipetted out and evaporated to give the product.