Chloride → HCID 178473719, compound

Participants

Reaction Steps

The starting material can be obtained by hydrogenation of 4-oxo-5-methoxy-1,4-dihydro-quinoline-2-acetic acid methyl ester to give 4-oxo-5-methoxy-1,2,3,4-tetrahydroquinoline-2-acetic acid methyl ester, saponification to give the free acid, acetylation to give 1-acetyl-4-oxo-5-methoxy-1,2,3,4-tetrahydro-quinoline-2-acetic acid, ether splitting by means of HBr/acetic acid, reaction into the chloride, Rosenmund reduction to give 1-acetyl-4-oxo-5-hydroxy-1,2,3,4-tetrahydro-quinoline-2-acetaldehyde, condensation with 2-phenyl-2-thiazolin-5-one to give 2-phenyl-4-[2-(1-acetyl-4-oxo-5-hydroxy-1,2,3,4-tetrahydro-2-quinolyl)-ethylidene]-2-thiazolin-5-one, condensation with acetonedicarboxylic acid monomethyl ester-monoamide to give 4-thiobenzamido-1,4,4a,5,5a,6,11,12-octahydro-3,10,12-trihydroxy-6-acetyl-1,11-dioxo-6-aza-naphthacene-2-carboxamide (mixture of stereoisomers), epimerization with pyridine to give 4-de-dimethylamino-4-thiobenzamido-6-acetyl-12a-de-hydroxy-6-aza-tetracycline and hydroxylation.

Provenance & Evidence