Tetrahedron Letters p. 7107 - 7110 (1994)
Update date:2022-07-30
Topics:
Moreira, Rui
Mendes, Eduarda
Calheiros, Teresa
Bacelo, Maria J.
Iley, Jim
N-Alkyl-N-chloromethylamides 2, prepared from secondary amides, paraformaldehyde and chlorotrimethylsilane, react readily with carboxylate anions to generate the corresponding tertiary N-acyloxymethylamides 3 in good yield; the latter give rise to the parent carboxylic acids in aqueous media at pH 7.4 and 37 deg C with half-lives between ca. 1 min and 42 h.
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