November 2010
http://www.ispharm.com
 Protected amino acids

Protected amino acids are used in chiral pool synthesis as antiomerically-pure building blocks. These materials have applications in peptide synthesis, medicine and drug delivery.

 Synthesis of protected amino acids.

1.

SOCl2 was added dropwise to a cooled solution of (S)-pyroglutamic acid in MeOH. After stirring for 2 h at RT, the solution was evaporated and the residue dissolved in CH2Cl2,washed with aq NaHCO3 and brine. Evaporation of the organic phase gave methyl(S)-pyroglutamate as a crude oil (yield, 87%). A solution of this crude ester, Boc2O and DMAP in MeCN was stirred for 1 h, and the residue obtained after removal of the solvent was purified by filtration on a short silica gel column using a gradient of EtOAc (0-50%) in CH2Cl2. Fractions positively detected with TDM reagent were collected, evaporated and gave 2 (yield,98%).

2.

To a solution of Nα-Cbz-amino acid derivative and sodium bicarbonate dissolved in water was added a solution of Fmoc-Cl in THF. The reaction mixture was stirred for 3 h at room temperature. After evaporation of THF, the aqueous phase was extracted with dichloromethane. The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure to give pure product.

 The application of protected amino acids

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