HCID 21435235, compound → HCID 21435204, compound
Reaction equation
[C:1]([C:4]([CH:7]1[CH2:16][C:15](=[O:17])[C:14]2[C:9](=[CH:10][C:11]([O:20]C)=[CH:12][C:13]=2[O:18]C)[O:8]1)([CH3:6])[CH3:5])(=[O:3])[NH2:2].Br.C(O)(=O)C>>[C:1]([C:4]([CH:7]1[CH2:16][C:15](=[O:17])[C:14]2[C:9](=[CH:10][C:11]([OH:20])=[CH:12][C:13]=2[OH:18])[O:8]1)([CH3:6])[CH3:5])(=[O:3])[NH2:2]Participants
Procedure
5,5-Dimethyl-8-hydroxy-6-oxatetracycline is obtained analogously from 5,5-dimethyl-8-benzyloxy-10-0-benzyl-6-oxatetracycline [obtainable by reaction of 2-(1-carbamoyl-1-methylethyl)-5,7-dimethoxy-4-chromanone with HBr/acetic acid to give 2-(1-carbamoyl-1-methylethyl)-5,7-dihydroxy-4-chromanone, benzylation, conversion into the nitrile, reaction with Raney nickel to give 2-(1-formyl-1-methylethyl)-5,7-dibenzyloxy-4-chromanone, condensation with 2-phenyl-2-thiazolin-5-one to give 2-phenyl-4-[2-methyl-2-(5,7-dibenzyloxy-chroman-4-on-2-yl)-propylidene]-2-thiazolin-5-one, condensation with acetonedicarboxylic acid monomethyl ester-monoamide and subsequent epimerization with pyridine to give 4-de-dimethylamino-4-thiobenzamido-5,5-dimethyl-8-benzyloxy-10-0-benzyl-12a-dehydroxy-6-oxatetracycline and 12a-hydroxylation, splitting off the thiobenzoyl group and methylation].
Workup
- custom5,5-Dimethyl-8-hydroxy-6-oxatetracycline is obtained analogously from 5,5-dimethyl-8-benzyloxy-10-0-benzyl-6-oxatetracycline [obtainable
Sources & evidence
- ORD record
- ord-9181be4c42fa4b28aa97427e002155d0
- Source dataset
- uspto-grants-1977_05
- Patent number
- US04024272
Reaction notes
Loading…