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Deprotection of t-Butyl Esters of Amino Acid Derivatives by Nitric Acid in Dichloromethane

✍ Scribed by Paolo Strazzolini; Massimo Scuccato; Angelo G Giumanini

Book ID
104202688
Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
163 KB
Volume
56
Category
Article
ISSN
0040-4020

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✦ Synopsis

AbstractÐThe extension of the deprotection procedure of t-butylated carboxyl function using HNO 3 in CH 2 Cl 2 to a number of appropriately selected N-Z-derivatives of natural amino acid esters was investigated. The method was found to work effectively with alanine, phenylalanine, serine and the dipeptide aspartame, but the reagent brought about a number of unwanted transformations with tyrosine, methionine and tryptophan. Suitable protection of functions present in the latter ones allowed selective ester dealkylation, but tyrosine underwent unavoidable fast preliminary ring nitration.

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Enantioselective syntheses of optically active or-amino acids from glycine t-butyl ester through Schiff base employing (+)-N-alkyl-10-camphorsulfonamides as chiral auxiliaries were described. Methylation of Schiff base 5 gave high asymmetric inductions, whereas ethylation, allylation and benzylation