- RESOLUTION OF α-METHYL AMINO ESTERS BY CHYMOTRYPSIN
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The resolution of DL-α-MeTrp-OMe HCl, DL-α-MePhe-OMe HCl and DL-α-Me-pF-Phe-OMe HCl have been achieved using α-chymotrypsin at pH 5.0.
- Anantharamaiah, G. M.,Roeske, Roger W.
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- Tetrahydro-pyrrolo-[2,3-b]indole-1,2,8-tricarboxylic acid ester in the enantiospecific preparation of α-methyltryptophan: Application in the preparation of carbon-14 labeled PD 145942 and PD 154075
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[2R-(2α,3aβ,8aβ)]-2,3,3a,8a-Tetrahydro-pyrrolo[2.3-b]indole-1,2,8 -tricarboxylic acid-1,8-dibenzyl ester 2-methyl ester, its [2S-(2β,3aα,8aα)]-isomer, and the tribenzyl ester analogs were prepared. From these [2,3-b]indole-1,2,8-tricarboxylic acid esters we accomplished a simple, high yielding preparation of enantiopure α-methyltryptophan and methyl ester derivatives. Using this protocol, we inexpensively made (R)-α-[14C]methyltryptophan methyl ester, and in subsequent reactions converted it into [1-(2-hydroxy-cyclohexylcarbamoyl)-2-(1H-indol-3-yl)-1 -[14C]methylethyl]carbamic acid adamantan-2-yl ester (PD 145942) and [2-(1H-indole-3-yl)-1-[14C]methyl-1(1-phenyl-ethylcarbamoyl)-ethyl]carbamic acid benzofuran-2-yl methyl ester (PD 154075). Both of these compounds are drug candidates in preclinical study for the treatment of anxiety and emesis respectively.
- Ekhato, I. Victor,Huang, Yun
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p. 1019 - 1038
(2007/10/03)
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