Process for antibiotic FR 1923 and related compounds
US4158004A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Nov 5, 1976 |
| Grant date | Jun 12, 1979 |
| Priority date | — |
| Expiry date | Nov 5, 1996 |
Classification
- Technology area (CPC Y)Emerging Cross-Sectional Technologies
- CPC primaryY02P20/55
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
Process for 1-[.alpha.-(carboxy)-4-hydroxy or protected-hydroxybenzyl]-3-acylamidoazetidin-2-one esters, useful intermediates for preparing antibiotic FR 1923, comprising the ring opening of a 2-acyl-3,3-dialkyl-7-oxo-.alpha.-[4-(protected-hydroxyphenyl]-4-thia-2,6-d iazabicyclo[3.2.0]heptane-6-acetic acid, ester sulfoxide with a sulfonic acid and heat to provide a 3-acylamido-4-(2-oxaalkylthio)azetidin-2-one ester which on treatment with sulfuryl chloride affords a reaction product mixture that is then reduced with an organo tin hydride, e.g., tri(n-butyl)tin hydride, to the product. N-Deacylation of the 3-acylamido group followed by acylation with the 3-acyl portion of FR 1923, deblocking of the amino-protecting group and deesterification affords FR 1923.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.