MW‐Enhanced High‐Speed Deprotection of Boc Group Using p‐TsOH and Concommitant Formation of N‐Me‐Amino Acid Benzyl Ester p‐TsOH Salts

References

• Greene , T. W. and Wuts , P. G. M. 1999 . Protective Groups in Organic Synthesis , 3rd ed. New York : Wiley .
   Google Scholar
• Kimura , T. , Takai , M. , Masui , Y. , Morikawa , T. and Sakakibara , S. 1981 . Biopolymers , 20 : 1823
   PubMed Web of Science ®Google Scholar
• Merrifield , R. B. 1964 . Biochemistry , 3 : 1385
   PubMed Web of Science ®Google Scholar
• Atherton , E. , Fox , H. , Harkiss , D. , Logan , C. J. , Sheppard , R. C. and Williams , B. J. 1978 . J. Chem. Soc., Chem. Commun. , : 537
   Google Scholar
• Podlech , J. 2002 . Methods of Organic Chemistry (Houben‐Weyl): Synthesis of Peptides and Peptidomimetics , 4th ed. Edited by: Goodman , M. Vol. E22a , 86 Stuttgart, , New York : Thieme .
   Google Scholar
• Hiskey , R. G. , Beachman , L. M. III , Matl , V. G. , Smith , J. N. , Williams , E. B. Jr. , Thomas , A. M. and Wolters , E. T. 1971 . J. Org. Chem. , 36 : 488
   PubMed Web of Science ®Google Scholar
• Sivanandaiah , K. M. , Suresh Babu , V. V. and Gangadhar , B. P. 1996 . Tetrahedron Lett. , 37 : 5989
   Google Scholar
• Kaiser , E. , Tam , J. P. Sr. , Kubiak , T. M. and Merrifield , R. B. 1988 . Tetrahedron Lett. , 29 : 303
   Web of Science ®Google Scholar
• Lott , R. S. , Chauhan , V. S. and Stammer , C. H. 1979 . J. Chem. Soc., Chem. Commun. , : 95
   Google Scholar
• Fuji , N. , Okata , A. , Ikemura , O. , Akaji , K. , Funakoshi , S. , Hayashi , Y. , Kuroda , Y. and Yajima , H. 1987 . J. Chem. Soc., Chem. Commun. , : 274
   Google Scholar
• Zhang , A. J. , Russel , D. H. , Zhu , J. and Burgess , K. 1998 . Tetrahedron Lett. , 39 : 7439
   Web of Science ®Google Scholar
• Bose , D. S. and Lakshminarayana , V. 1998 . Tetrahedron Lett. , 39 : 5631
   Google Scholar
• Chauvette , R. R. , Pennington , P. A. , Ryan , C. W. , Cooper , R. D. G. , Jose , F. L. , Wright , I. G. , van Heyningen , E. M. and Huffinan , G. W. 1971 . J. Org. Chem. , 36 : 1259
   PubMed Web of Science ®Google Scholar
• Goodacre , J. , Ponsford , R. J. and Stirling , I. 1975 . Tetrahedron Lett. , : 3609
   Google Scholar
• Yajima , H. , Ogawa , H. , Fujii , N. and Funakoshi , S. 1977 . Chem. Pharm. Bull. , 25 : 740
   Google Scholar
• Suzuki , K. , Endo , N. , Nitta , K. and Sasaki , Y. 1978 . Chem. Pharm. Bull. , 26 : 2198
   Web of Science ®Google Scholar
• Brinkmann , H. R. , Landi , J. J. Jr. , Paterson , J. B. and Stone , P. J. 1991 . Synth. Commun. , 21 : 459
   Google Scholar
• Varma , R. S. Green Chemistry: Challenging Perspectives Edited by: Tundo , P. and Anastas , P. T. Vol. 221 , Oxford : Oxford University Press . For recent reports on MW irradiation, see (a)
   Google Scholar
• Lindstrom , P. , Tierney , J. , Wathey , B. and Westman , J. 2001 . Tetrahedron , 57 : 9225
   Web of Science ®Google Scholar
• Das , S. K. 2004 . Synlett , : 915
   Google Scholar
• Daga , M. C. , Taddei , M. and Varchi , G. 2001 . Tetrahedron Lett. , 42 : 5191 [Catalytic transfer hydrogenation using iso‐propanol as hydrogen donor under MW irradiation (for 2 min of 3–5 cycles) has been performed to rapidly deprotect N‐Cbz and N‐Bn derivatives (with 90–95% yield)]
   Google Scholar
• Paul , S. , Gupta , M. , Gupta , R. and Loupy , A. 2001 . Tetrahedron Lett. , 42 : 3827 [p‐TsOH was demonstrated as a superior solid support for the solvent‐free synthesis of pyrazolo[3,4‐6]quinolines and pyrazolo[3,4‐c]pyrazoles]
   Web of Science ®Google Scholar
• Wenger , R. M. 1985 . Angew. Chem, Int. Ed. Engl. , 24 : 77
   Web of Science ®Google Scholar
• Wenger , R. M. 1983 . Helv. Chim. Acta , 66 : 2672
   Google Scholar
• Coste , J. , Frerot , E. and Jouin , P. 1994 . J. Org. Chem. , 59 : 2437
   Web of Science ®Google Scholar
• Akaji , K. , Hayashi , Y. , Kiso , Y. and Kuriyama , N. 1999 . J. Org. Chem. , 64 : 405
   Web of Science ®Google Scholar
• Li , P. and Xu , J.‐C. 2000 . Tetrahedron , 56 : 8119
   Web of Science ®Google Scholar
• Wang , S. S. , Gisin , B. F. , Winter , D. P. , Makofske , R. , Kulesha , I. D. , Tzougraki , C. and Meienhofer , J. 1977 . J. Org. Chem. , 42 : 1286
   PubMed Web of Science ®Google Scholar
• Vasanthakumar , G.-R. , Patil , B. S. and Suresh Babu , V. V. 2002 . Lett. Peptide Sci. , 9 : 207 [For rapid synthesis of amino acid benzyl ester p‐TsOH salts using corresponding amino acid, benzyl alcohol, and p‐TsOH under MW irradiation]
   Google Scholar