Cefmenoxime
Template:Short description Template:Cs1 config Template:Short description <templatestyles src="Infobox drug/styles.css"/> Script error: No such module "Infobox".Template:Template otherScript error: No such module "TemplatePar".{{Infobox drug/maintenance categoriesTemplate:Yesno | drug_name = | INN = | _drugtype =
| _has_physiological_data= | _has_gene_therapy=
| vaccine_type= | mab_type= | _number_of_combo_chemicals=Script error: No such module "ParameterCount". | _vaccine_data= | _mab_data= | _mab_vaccine_data= | _mab_other_data=161795O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)C(=N\OC)/c3nc(sc3)N)CSc4nnnn4C)C(=O)O1S/C16H17N9O5S3/c1-24-16(20-22-23-24)33-4-6-3-31-13-9(12(27)25(13)10(6)14(28)29)19-11(26)8(21-30-2)7-5-32-15(17)18-7/h5,9,13H,3-4H2,1-2H3,(H2,17,18)(H,19,26)(H,28,29)/b21-8-/t9-,13-/m1/s1HJJDBAOLQAWBMH-YCRCPZNHSA-NTemplate:StdinchiciteTemplate:Stdinchicite | _combo_data= | _physiological_data= | _clinical_data=Template:Drugs.com Intramuscular, intravenousJ01Template:ATC, Template:ATC | _legal_data=
| _other_data=(6R,7R)-7-{[(2E)-2-(2-amino-1,3-thiazol-4-yl)-
2-methoxyimino-acetyl]amino}-3-[(1-methyltetrazol-
5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]
oct-2-ene-2-carboxylic acid
| _image_0_or_2 = Cefmenoxime.svg | _image_LR =
| _datapage = Cefmenoxime (data page) | _vaccine_target=_type_not_vaccine | _legal_all= | _ATC_prefix_supplemental=J01Template:ATC, Template:ATC | _has_EMA_link = | CAS_number=65085-01-0 | PubChem=9570757 | ChemSpiderID=7845223 | ChEBI=55490 | ChEMBL=1201224 | DrugBank=DB00267 | KEGG=D07641 | _hasInChI_or_Key=yes | UNII=KBZ4844CXN | _hasJmol02 = |_hasMultipleCASnumbers = |_hasMultiplePubChemCIDs = |_hasMultipleChEBIs =
| _countSecondIDs=Script error: No such module "ParameterCount". | _countIndexlabels=Script error: No such module "ParameterCount". | _trackListSortletter= |QID = |QID2 = |Verifiedfields=changed |Watchedfields= |verifiedrevid=460023267}}
Cefmenoxime is a third-generation cephalosporin antibiotic.[1]
Synthesis
The alkylation of ethyl 2-hydroxyimino-3-oxobutanoate (1) with dimethylsulfate gives ethyl (2Z)-2-methoxyimino-3-oxo-butanoate (2). Halogenation with molecular bromine leads to ethyl 4-bromo-2-methoxyimino-3-oxobutanoate (3). Treatment with thiourea gives ethyl (Z)-2-(2-amino-4-thiazolyl)-2-methoxyiminoacetate (4) which is reacted with chloroacetyl chloride to give the amide (5). Saponification with potassium hydroxide gives (6) which is halogenated with phosphorus pentachloride to (7). Amide formation with the cephalosporin intermediate (8) then gives (9). Removal of the protecting group with benzyltriethylammonium bromide yields (10). The tert-butyl ester was deprotected with trifluoroacetic acid to give (11). Lastly, thioether formation with 5-mercapto-1-methyltetrazole (12) completes the synthesis of cefmenoxime.[2][3][4][5]
References
<templatestyles src="Reflist/styles.css" />
- ↑ Script error: No such module "Citation/CS1".
- ↑ <templatestyles src="Citation/styles.css"/>Template:Citation/make link, Ochiai M, Okada T, Aki O, Morimoto A, Kawakita K, Matsushita Y, "Thiazolylacetamido cephalosporin type compounds", issued Script error: No such module "auto date formatter"., assigned to Takeda Pharmaceutical Co Ltd.Script error: No such module "Check for unknown parameters".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
Script error: No such module "Check for unknown parameters".
Further reading
<templatestyles src="Refbegin/styles.css" />
- Script error: No such module "Citation/CS1".
- Script error: No such module "Citation/CS1".
- Script error: No such module "Citation/CS1".
External links
Script error: No such module "Navbox".