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Synthesis 2001(13): 1985-1988
DOI: 10.1055/s-2001-17710
DOI: 10.1055/s-2001-17710
PAPER
© Georg Thieme Verlag Stuttgart · New York
Rapid Procedure for N-Phthaloylation of α-Amino Carboxamides, α-Amino Alcohols, α-Amino Esters and Dipeptide Derivatives
Weitere Informationen
Received
15 May 2001
Publikationsdatum:
11. August 2004 (online)
Publikationsverlauf
Publikationsdatum:
11. August 2004 (online)
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Abstract
A rapid, one-pot synthesis and mild procedure for the N-phthaloylation of α-amino carboxamides is described. In acetonitrile, these derivatives react with mono-methylphthalate in the presence of BOP and i-Pr2NEt to afford the intermediate N α-[(o-methoxycarbonyl)benzoyl]amino carboxamides, which undergo rapid cyclization in the presence of aqueous sodium carbonate to afford the corresponding N α-phthaloylamino carboxamides in excellent yields. The reaction also works efficiently with α-amino esters, α-amino alcohols and dipeptide esters or amides.
Key words
phthaloyl protection - α-amino carboxamides - mono-methylphthalate - α-amino alcohols - cyclization
- 1
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References
In both cases, the ratio l/d was >99:1.