Process for antibiotic FR 1923 and related compounds

Details Process for antibiotic FR 1923 and related compounds Process for antibiotic FR 1923 and related compounds

1976-11-05

1979-06-12

Daus, Donald G.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260307F, 2603067C, C07D20108, C07D20508

Patent

active

041580044

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.

REFERENCES:
patent: 3991069 (1976-11-01), Barton et al.
Baldwin et al., I, J. Amer. Chem. Soc. 97, 5957-5958 (1975).
Baldwin et al. II, J. Amer. Chem. Soc. 98, 3045 (1976).
Fujisawa, Derwent 06757X104 . NL7508-008.
Fujisawa, Derwent 11208X107 B03.

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