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Mono-esterification of N-protected di-acids aspartic and glutamic by chloroformate activation.

✍ Scribed by P. Jouin; B. Castro; C. Zeggaf; A. Pantaloni; J.P. Senet; S. Lecolier; G. Sennyey

Book ID: 104227149
Publisher: Elsevier Science
Year: 1987
Tongue: French
Weight: 201 KB
Volume: 28
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)95388-7

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✦ Synopsis

Mono-esters of N-protected dl-acids aspartlc end glutemic ere prepered by a one-pot ectlvetlon with elkyl chloroformates or isopropenyl chloroformate end en eddltfonnel elcohol. This process Involves the lntermedlete lnternel enhydrlde formetion. With respect to the mono-esterlflcatlon of N-protected aspartlc 1 or glutamlc dlacld 2. the most sultable reactlon already described was a multi-steps procedure that involved the partlally regioselectlve openlng of the preformed Internal anhydrlde 3 or 4, ieadlng predomlnantly to the a-isomer 7a or 8a I. The Internal anhydrlde was mostly prepared from acetlc enhydrlde 2 or oarbodllmlde b actlvatlon of the N-protected dl-4 Melenhofer. J. The peptldes, Anelysls, Synthesis, i3lology.

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