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filingDate 1996-01-29-04:00^^<http://www.w3.org/2001/XMLSchema#date>
grantDate 1997-09-09-04:00^^<http://www.w3.org/2001/XMLSchema#date>
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publicationDate 1997-09-09-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber US-5665598-A
titleOfInvention Synthesis of chiral N-protected-α-substituted-glycine free acids by zinc-mediated addition of organic halide to glycine cation equivalent
abstract A method is described for synthesis of N-Boc-L-propargylglycine, a key intermediate used in the preparation of high-potency, orally-active renin inhibitors. This method involves reaction of an organic halide with a glycine cation equivalent, such as methyl N-Boc-2-acetoxyglycine, in the presence of zinc dust to give Boc-protected amino acid derivatives in high yield. Typically useful organic halides are allylic, benzylic and propargylic halides. Resolution of methyl N-Boc-propargylglycine with alpha -chymotrypsin provides N-Boc-L-propargylglycine in high yield.
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