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CAS 957-68-6
(6R,7R)-3-(Acetoxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Codes: Ceftazidime-011, Cefoselis Sulfate-037, Cefonicid-011, Cefonicid-016, Cefcamate Pivoxil Hydrochloride-024
Application context (from source-drug indications)
CystitisAvibactam Sodium/CeftazidimeCholecystitisAvibactam Sodium/CeftazidimePeritonitisAvibactam Sodium/CeftazidimeIntra-abdominal infectionAvibactam Sodium/CeftazidimeLiver abscessAvibactam Sodium/CeftazidimeSepsisAvibactam Sodium/CeftazidimeBacterial infectionCeftazidime/Tazobactam SodiumRespiratory tract infectionCeftazidime/Tazobactam SodiumUrinary tract infectionCeftazidime/Tazobactam SodiumBacterial infectionCefoselis SulfateBacterial infectionCeftazidimeGram-positive bacterial infectionCeftazidimeGram-negative bacterial infectionCeftazidimeGynaecological disorderCeftazidimeIntra-abdominal infectionCeftazidimeOsteoarthritisCeftazidimeBacterial infectionCefonicid SodiumBacterial infectionCefcamate Pivoxil Hydrochloride
Source drugs (routes using this intermediate)
| Drug | Tier | Expiry |
|---|---|---|
| Avibactam Sodium/Ceftazidime | Tier C — Watch / trade | - |
| Ceftazidime/Tazobactam Sodium | Tier C — Watch / trade | - |
| Cefoselis Sulfate | Tier C — Watch / trade | - |
| Ceftazidime | Tier C — Watch / trade | - |
| Cefonicid Sodium | Tier C — Watch / trade | - |
| Cefcamate Pivoxil Hydrochloride | Tier C — Watch / trade | - |
Position in synthesis routes (up/downstream chain)
Ordered by route registration; left → right is the synthesis direction. The highlighted node is the current CAS; others link to their own profiles.
ethyl 3-oxobutanoate→Ethyl nitrite→Non-denatured ethanol→ethyl (E)-2-(hydroxyimino)-3-oxobutanoate→thiourea→ethyl (Z)-2-(2-aminothiazol-4-yl)-2-(hydroxyimino)acetate→Ethyl (2Z)-(hydroxyimino)[2-[(triphenylmethyl)amino]-1,3-thiazol-4-yl]acetate→tert-Butyl 2-bromo-2-methylpropionate→tert-Butyl 2-[[(Z)-(2-ethoxy-2-oxo-1-[2-[(triphenylmethyl)amino]-1,3-thiazol-4-yl]ethylidene)amino]oxy]-2-methylpropanoate→(2Z)-[[(1-tert-Butoxy-2-methyl-1-oxopropan-2-yl)oxy]imino][2-[(triphenylmethyl)amino]-1,3-thiazol-4-yl]acetic acid→(6R,7R)-3-(Acetoxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid→(6R,7R)-3-[(Acetyloxy)methyl]-7-[[(2Z)-2-[[(1-tert-butoxy-2-methyl-1-oxopropan-2-yl)oxy]imino]-2-[2-[(triphenylmethyl)amino]-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid→(6R,7R)-3-[(Acetyloxy)methyl]-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[[(2-carboxypropan-2-yl)oxy]imino]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid→pyridine
(6R,7R)-3-(Acetoxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid→Trimethylsilyl 7-(trimethylsilylamino)cephalosporanate→Trimethylsilyl (6R,7R)-3-(iodomethyl)-8-oxo-7-[(trimethylsilyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate→Pyridine→1-[[(6R,7R)-8-Oxo-7-[(trimethylsilyl)amino]-2-[[(trimethylsilyl)oxy]carbonyl]-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]pyridin-1-ium iodide→(6R,7R)-7-Amino-8-oxo-3-(pyridinium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate dihydrochloride→2-[[(Z)-[1-(2-Amino-1,3-thiazol-4-yl)-2-[(1,3-benzothiazol-2-yl)sulfanyl]-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid→tert-Butyl 2-[[(Z)-[1-(2-amino-1,3-thiazol-4-yl)-2-[(1,3-benzothiazol-2-yl)sulfanyl]-2-oxoethylidene]amino]oxy]-2-methylpropanoate→(6R,7R)-7-[[(2Z)-2-(2-Amino-1,3-thiazol-4-yl)-2-[[(1-tert-butoxy-2-methyl-1-oxopropan-2-yl)oxy]imino]acetyl]amino]-8-oxo-3-[(pyridin-1-ium-1-yl)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylat e
ethyl 3-oxobutanoate→Ethyl nitrite→Non-denatured ethanol→ethyl (E)-2-(hydroxyimino)-3-oxobutanoate→thiourea→ethyl (Z)-2-(2-aminothiazol-4-yl)-2-(hydroxyimino)acetate→Ethyl (2Z)-(hydroxyimino)[2-[(triphenylmethyl)amino]-1,3-thiazol-4-yl]acetate→tert-Butyl 2-bromo-2-methylpropionate→tert-Butyl 2-[[(Z)-(2-ethoxy-2-oxo-1-[2-[(triphenylmethyl)amino]-1,3-thiazol-4-yl]ethylidene)amino]oxy]-2-methylpropanoate→(2Z)-[[(1-tert-Butoxy-2-methyl-1-oxopropan-2-yl)oxy]imino][2-[(triphenylmethyl)amino]-1,3-thiazol-4-yl]acetic acid→(6R,7R)-3-(Acetoxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid→(6R,7R)-3-[(Acetyloxy)methyl]-7-[[(2Z)-2-[[(1-tert-butoxy-2-methyl-1-oxopropan-2-yl)oxy]imino]-2-[2-[(triphenylmethyl)amino]-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid→(6R,7R)-3-[(Acetyloxy)methyl]-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[[(2-carboxypropan-2-yl)oxy]imino]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid→pyridine
(6R,7R)-3-(Acetoxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid→Trimethylsilyl 7-(trimethylsilylamino)cephalosporanate→Trimethylsilyl (6R,7R)-3-(iodomethyl)-8-oxo-7-[(trimethylsilyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate→Pyridine→1-[[(6R,7R)-8-Oxo-7-[(trimethylsilyl)amino]-2-[[(trimethylsilyl)oxy]carbonyl]-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]pyridin-1-ium iodide→(6R,7R)-7-Amino-8-oxo-3-(pyridinium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate dihydrochloride→2-[[(Z)-[1-(2-Amino-1,3-thiazol-4-yl)-2-[(1,3-benzothiazol-2-yl)sulfanyl]-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid→tert-Butyl 2-[[(Z)-[1-(2-amino-1,3-thiazol-4-yl)-2-[(1,3-benzothiazol-2-yl)sulfanyl]-2-oxoethylidene]amino]oxy]-2-methylpropanoate→(6R,7R)-7-[[(2Z)-2-(2-Amino-1,3-thiazol-4-yl)-2-[[(1-tert-butoxy-2-methyl-1-oxopropan-2-yl)oxy]imino]acetyl]amino]-8-oxo-3-[(pyridin-1-ium-1-yl)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylat e
(6R,7R)-3-(Acetoxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid→Trimethylsilyl (6R,7R)-3-(iodomethyl)-8-oxo-7-[(trimethylsilyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate→2-[5-(Formylamino)-1H-pyrazol-1-yl]ethyl formate→(6R,7R)-7-Amino-3-[[5-amino-1-(2-hydroxyethyl)-1H-pyrazol-2-ium-2-yl]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate hydrochloride→S-(benzo[d]thiazol-2-yl) (Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate→(6R,7R)-3-[[5-Amino-1-(2-hydroxyethyl)-1H-pyrazol-2-ium-2-yl]methyl]-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
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