Synthesis of chiral N-protected-.alpha.-substituted-glycine free acids by zinc-mediated addition of organic halide to glycine cation equivalent
US5665598A · kind A · utility
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Key dates
| Filing date | Jan 29, 1996 |
| Grant date | Sep 9, 1997 |
| Priority date | — |
| Expiry date | Jan 29, 2016 |
Classification
- Technology area (CPC Y)Emerging Cross-Sectional Technologies
- CPC primaryY02P20/55
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
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.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.