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CAS 60845-81-0
ethyl (Z)-2-(2-aminothiazol-4-yl)-2-(hydroxyimino)acetate2(Z)-(2-Aminothiazol-4-yl)-2-(hydroxyimino)acetic acid ethyl ester
Codes: Ceftazidime-006, Ceftazidime-027
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 infectionCeftazidimeGram-positive bacterial infectionCeftazidimeGram-negative bacterial infectionCeftazidimeGynaecological disorderCeftazidimeIntra-abdominal infectionCeftazidimeOsteoarthritisCeftazidime
Source drugs (routes using this intermediate)
| Drug | Tier | Expiry |
|---|---|---|
| Avibactam Sodium/Ceftazidime | Tier C — Watch / trade | - |
| Ceftazidime/Tazobactam Sodium | Tier C — Watch / trade | - |
| Ceftazidime | 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
2-Methylpropionic acid→2-Bromo-2-methylpropanoic acid→t-Butyl 2-bromo isobutyrate→2(Z)-(2-Aminothiazol-4-yl)-2-(hydroxyimino)acetic acid ethyl ester→tert-Butyl 2-([(Z)-[1-(2-amino-1,3-thiazol-4-yl)-2-ethoxy-2-oxoethylidene]amino]oxy)-2-methylpropanoate→(2Z)-(2-Amino-1,3-thiazol-4-yl)[[(1-tert-butoxy-2-methyl-1-oxopropan-2-yl)oxy]imino]acetic acid→2-([[(1Z)-1-(2-Amino-1,3-thiazol-4-yl)-2-chloro-2-oxoethylidene]amino]oxy)-2-methylpropanoic acid hydrochloride→(6R,7R)-7-Amino-8-oxo-3-(pyridinium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate hydroiodide
(2Z)-(2-Amino-1,3-thiazol-4-yl)[[(1-tert-butoxy-2-methyl-1-oxopropan-2-yl)oxy]imino]acetic acid→(6R,7R)-7-Amino-8-oxo-3-(pyridinium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate hydroiodide→2(Z)-(2-Aminothiazol-4-yl)-2-(hydroxyimino)acetic acid ethyl ester→tert-Butyl 2-bromo-2-methylpropionate<-fgf->2-Bromo-2-methylpropionic acid tert-butyl ester→Sodium (2Z)-(2-amino-1,3-thiazol-4-yl)(hydroxyimino)acetate→tert-Butyl 2-[[(Z)-[1-(2-amino-1,3-thiazol-4-yl)-2-[[(4-methylphenyl)sulfonyl]oxy]-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→Potassium (2Z)-(2-amino-1,3-thiazol-4-yl)(hydroxyimino)acetate→Lithium (2Z)-(2-amino-1,3-thiazol-4-yl)(hydroxyimino)acetate
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
2-Methylpropionic acid→2-Bromo-2-methylpropanoic acid→t-Butyl 2-bromo isobutyrate→2(Z)-(2-Aminothiazol-4-yl)-2-(hydroxyimino)acetic acid ethyl ester→tert-Butyl 2-([(Z)-[1-(2-amino-1,3-thiazol-4-yl)-2-ethoxy-2-oxoethylidene]amino]oxy)-2-methylpropanoate→(2Z)-(2-Amino-1,3-thiazol-4-yl)[[(1-tert-butoxy-2-methyl-1-oxopropan-2-yl)oxy]imino]acetic acid→2-([[(1Z)-1-(2-Amino-1,3-thiazol-4-yl)-2-chloro-2-oxoethylidene]amino]oxy)-2-methylpropanoic acid hydrochloride→(6R,7R)-7-Amino-8-oxo-3-(pyridinium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate hydroiodide
(2Z)-(2-Amino-1,3-thiazol-4-yl)[[(1-tert-butoxy-2-methyl-1-oxopropan-2-yl)oxy]imino]acetic acid→(6R,7R)-7-Amino-8-oxo-3-(pyridinium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate hydroiodide→2(Z)-(2-Aminothiazol-4-yl)-2-(hydroxyimino)acetic acid ethyl ester→tert-Butyl 2-bromo-2-methylpropionate<-fgf->2-Bromo-2-methylpropionic acid tert-butyl ester→Sodium (2Z)-(2-amino-1,3-thiazol-4-yl)(hydroxyimino)acetate→tert-Butyl 2-[[(Z)-[1-(2-amino-1,3-thiazol-4-yl)-2-[[(4-methylphenyl)sulfonyl]oxy]-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→Potassium (2Z)-(2-amino-1,3-thiazol-4-yl)(hydroxyimino)acetate→Lithium (2Z)-(2-amino-1,3-thiazol-4-yl)(hydroxyimino)acetate
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
2-Methylpropionic acid→2-Bromo-2-methylpropanoic acid→t-Butyl 2-bromo isobutyrate→2(Z)-(2-Aminothiazol-4-yl)-2-(hydroxyimino)acetic acid ethyl ester→tert-Butyl 2-([(Z)-[1-(2-amino-1,3-thiazol-4-yl)-2-ethoxy-2-oxoethylidene]amino]oxy)-2-methylpropanoate→(2Z)-(2-Amino-1,3-thiazol-4-yl)[[(1-tert-butoxy-2-methyl-1-oxopropan-2-yl)oxy]imino]acetic acid→2-([[(1Z)-1-(2-Amino-1,3-thiazol-4-yl)-2-chloro-2-oxoethylidene]amino]oxy)-2-methylpropanoic acid hydrochloride→(6R,7R)-7-Amino-8-oxo-3-(pyridinium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate hydroiodide
(2Z)-(2-Amino-1,3-thiazol-4-yl)[[(1-tert-butoxy-2-methyl-1-oxopropan-2-yl)oxy]imino]acetic acid→(6R,7R)-7-Amino-8-oxo-3-(pyridinium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate hydroiodide→2(Z)-(2-Aminothiazol-4-yl)-2-(hydroxyimino)acetic acid ethyl ester→tert-Butyl 2-bromo-2-methylpropionate<-fgf->2-Bromo-2-methylpropionic acid tert-butyl ester→Sodium (2Z)-(2-amino-1,3-thiazol-4-yl)(hydroxyimino)acetate→tert-Butyl 2-[[(Z)-[1-(2-amino-1,3-thiazol-4-yl)-2-[[(4-methylphenyl)sulfonyl]oxy]-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→Potassium (2Z)-(2-amino-1,3-thiazol-4-yl)(hydroxyimino)acetate→Lithium (2Z)-(2-amino-1,3-thiazol-4-yl)(hydroxyimino)acetate
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