Schönenberger, Helmut and Endres, W. (1976) Studies on the mode of action of local anesthetics. Part 8. Studies on the preparation of the enantiomeric N-phthalylaminocarboxylic acids. Pharmazie 31 (11), pp. 811-813.
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The D and L enantiomers of phthalyl amino acids I (R = Me, CHMe2, CHPh, indol-3-ylmethyl) and the L enantiomers of I [CH2CHMe2, CH2C6H4(OR)-p (R = H, CH2Ph)] were prepd. in 55.8-83.6% yields by treating phthalic anhydride with the appropriate amino acid for 3-5 min in boiling DMF. The influence of reaction times and R on racemization of L enantiomers of I are given. I were also prepd. in 20-91% yields by conducting the above reaction for 10-15 min at 150-160 Deg and in 20-68.2% yields by treating N-carboethoxyphthalimide with the appropriate amino acid in aq. Na2CO3.
|Additional information (public):||CAN 86:190429 34-2 Synthesis of Amino Acids, Peptides, and Proteins 2130-97-4P; 2419-38-7P; 4192-28-3P; 5123-55-7P; 6306-53-2P; 6306-54-3P; 29588-83-8P; 29588-94-1P; 32150-90-6P; 48208-26-0P; 62361-30-2P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 85-44-9; 22509-74-6 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with amino acids); 56-41-7; 60-18-4; 61-90-5; 63-91-2; 72-18-4; 73-22-3; 153-94-6; 338-69-2; 640-68-6; 673-06-3; 16652-64-5 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with phthalic anhydride)|
|Institutions:||Chemistry and Pharmacy > Institute of Pharmacy > Retired Professors > Prof. Schönenberger|
|Keywords:||Amino acids Role: SPN (Synthetic preparation), PREP (Preparation) (N-phthalyl, prepn. of, by substitution reactions of N-carbethoxyphthalimide, racemization in) Racemization (in substitution reactions of amino acids with N-carbethoxyphthalimide) Substitution reaction (of N-carbethoxyphthalimide with amino acids, racemization in) phthalyl amino acid substitution amino acid racemization carbethoxyphthalimide substitution racemization phthalyl amino acid|
|Subjects:||500 Science > 540 Chemistry & allied sciences|
|Refereed:||Yes, this version has been refereed|
|Created at the University of Regensburg:||Unknown|
|Deposited On:||19 Nov 2010 09:22|
|Last Modified:||19 Nov 2010 09:22|