Catalytic polymer-supported potassium thiophenolate in methanol as a method for the removal of ester, amide, and thioacetate protecting groups

Synlett

Volumn , Issue 4, 2004, Pages 675-678

  MacCoss, Rachel N ^a   Henry, Dara J ^a   Brain, Christopher T ^b   Ley, Steven V ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b Novartis Inst for Medical Sciences   (United Kingdom)

Author keywords

Deprotection; Polymer supported; Thiophenolate

Indexed keywords

ACETIC ACID; AMIDE; ESTER; METHANOL; POLYMER; POTASSIUM THIOPHENOLATE; THIOPHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; DEPROTECTION REACTION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; REACTION ANALYSIS;

EID: 1642408425     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-817786     Document Type: Article

References (10)

1. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley and Sons: New York, 1991.
2. Argonaut Technologies Catalog 2000, p. 53.
3. Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G. ; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 23, 3815.
4. For some recent applications see: (a) Jamieson, C.; Congreave, M. S.; Embiata-Smith, D. F.; Ley, S. V. Synlett 2000, 1603.
5. (b) Jamieson, C.; Congreave, M. S.; Embiata-Smith, D. F.; Ley, S. V.; Scicinski, J. J. Org. Process Res. Dev. 2002, 6, 823.
6. General Procedure: Protected compound (1.0 equiv) was dissolved in MeOH/THF (1:1) in a sealed vial and stirred with thiophenolate resin 1 (1.45 mmol/g, 0.2 equiv). The reaction was heated as described herein. When reaction was complete, the resin was removed by filtration and washed with THF. The combined washings were dried in vacuo. If starting material remained, the product was isolated by standard column chromatography.
7. Thiophenolate Resin: Polymer-supported thiophenol was shaken at r.t. under argon with potassium trimethylsilanolate in THF. After 2 d, the resin was rinsed with THF and dried in vacuo (1.45 mmol/g).
8. All compounds gave satisfactory spectroscopic data identical to those reported in the literature.
9. Wallace, O. B.; Springer, D. M. Tetrahedron Lett. 1998, 39, 2693.
10. 2 three times, and dried in vacuo before reusing.