L-Glutamic acid dibenzyl ester tosylate synthesis
- Product Name:L-Glutamic acid dibenzyl ester tosylate
- CAS Number:2791-84-6
- Molecular formula:C26H29NO7S
- Molecular Weight:499.58
56-86-0
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100-51-6
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2791-84-6
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Yield: 81%
Reaction Conditions:
in cyclohexane for 24 h;Reflux;
Steps:
General procedure for synthesis of 1a-1c:
General procedure: p-TsCl catalysed benzyl esterification of mono- and di- carboxylic acid is described in Scheme 1. For L-phenylalanine, since it contains monocarboxylic group, half equivalents of benzyl alcoholand p-TsCl were taken than those used for dicarboxylicamino acids l-aspartic acid and l-glutamic acid. Reaction mixture contained 1 gm (6.8 mmol) l-glutamic acid, 1.56gm (8.2 mmol) p-TsCl, 4 ml (38.6 mmol) benzyl alcoholand 20 ml (excess) cyclohexane. The reaction mixture wasrefluxed overnight under continuous stirring and progressof reaction was monitored through TLC. On completion,the reaction mixture was cooled to room temperature andethyl acetate was added till complete precipitation of products1a-1c. The precipitate obtained was filtered, washedwith cold ethyl acetate and dried to yield benzyl-protectedp-toluenesulfonate salts of respective amino acids.
References:
Hegde, Namita;Juvale, Kapil;Prabhakar, Bala [International Journal of Peptide Research and Therapeutics,2020,vol. 26,# 4,p. 2129 - 2135]
56-86-0
826 suppliers
$5.00/25g
104-15-4
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$133.00/500g
100-51-6
1405 suppliers
$5.00/100g
2791-84-6
157 suppliers
$7.00/5g