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Synthesis and decarboxylation of N-acyl-α-triphenylphosphonio-α-amino acids: a new synthesis of α-(N-acylamino)alkyltriphenylphosphonium salts

✍ Scribed by Roman Mazurkiewicz; Agnieszka Październiok-Holewa; Mirosława Grymel

Publisher
Elsevier Science
Year
2008
Tongue
French
Weight
103 KB
Volume
49
Category
Article
ISSN
0040-4039

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✦ Synopsis

4-Phosphoranylidene-5(4H)-oxazolones 1 undergo hydrolysis in THF in the presence of HBF 4 at room temperature to give N-acyl-atriphenylphosphonioglycines 3 (R 2 = H) in very good yields. 4-Alkyl-4-triphenylphosphonio-5(4H)-oxazolones 2 react with water in CH 2 Cl 2 /THF solution without any acidic catalyst at 0-5 °C in a few days yielding N-acyl-a-triphenylphosphonio-a-amino acids 3 (R 2 = Me) or a-(N-acylamino)alkyltriphenylphosphonium salt 4 (R 2 = CH 2 OMe). a-Triphenylphosphonio-a-amino acids 3, on heating up to 105-115 °C under reduced pressure (5 mmHg) or on treatment with diisopropylethylamine in CH 2 Cl 2 at 20 °C undergo decarboxylation to give the corresponding a-(N-acylamino)alkyltriphenylphosphonium salts 4, usually in very good yields.

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