2,3-cyclopentenopyridine
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
7-Aminocephalosporanic acid
cefpirome Sulfate
Conditions | Yield |
---|---|
With sulfuric acid for 0.0666667h; Time; Microwave irradiation; | 99% |
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
7-aminodesacetoxycephalosporanic acid
(Z)-7-[(2-amino-4-thiazolyl-2-methoxyiminoacetylamino)]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
With dmap; triethylamine In water; acetone at 20℃; for 3.5h; Time; | 98.5% |
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
Conditions | Yield |
---|---|
With sulphurous acid; triethylamine In dichloromethane at 0 - 5℃; Concentration; Large scale; | 98.3% |
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
di(benzothiazol-2-yl)disulfide
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; ozone In methanol at 44℃; for 1.5h; Concentration; Temperature; Large scale; | 97.5% |
sulphapyridine
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
Conditions | Yield |
---|---|
With pyridine; triethylamine In ethanol; dichloromethane at 20℃; Inert atmosphere; | 96% |
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
7-aminoceftrizine
ceftriaxone disodium
Conditions | Yield |
---|---|
Stage #1: (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate; 7-aminoceftrizine With triethylamine In methanol at -2 - 3℃; Stage #2: With sodium 2-ethylhexanoic acid In water; isopropyl alcohol at 26 - 30℃; for 2h; Product distribution / selectivity; | 95.5% |
With sodium metabisulfite; edetate disodium; triethylamine In ethanol; water at 1 - 3℃; for 3h; Time; | 91% |
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
7-Aminocephalosporanic acid
cefotaxime
Conditions | Yield |
---|---|
With TEA In dichloromethane at 20℃; for 1h; Substitution; | 95% |
With triethylamine In dichloromethane at 20℃; for 1h; | 95% |
Stage #1: (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate; 7-Aminocephalosporanic acid With triethylamine In methanol at 0 - 5℃; Stage #2: With hydrogenchloride In methanol; water at 0 - 5℃; for 1h; pH=2.3 - 2.5; | |
Stage #1: (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate; 7-Aminocephalosporanic acid With triethylamine In 1,2-dimethoxyethane at -5 - 0℃; Stage #2: With hydrogenchloride In 1,2-dimethoxyethane; water for 1h; pH=2.6 - 2.8; Product distribution / selectivity; |
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
7-aminoceph-3-em-4-carboxylic acid ester
Conditions | Yield |
---|---|
With diethylamine In dichloromethane; butan-1-ol at -5℃; for 12h; Solvent; Reagent/catalyst; Autoclave; Large scale; | 93.6% |
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid
Conditions | Yield |
---|---|
With triethylamine In ethanol at 20 - 25℃; Schotten-Baumann reaction; | 93% |
(6R,7R)-7-amino-3-[(1Z)-2-(4-methyl-5-thiazolyl)vinyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
diisopropylamine
Conditions | Yield |
---|---|
Stage #1: (6R,7R)-7-amino-3-[(1Z)-2-(4-methyl-5-thiazolyl)vinyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate With dmap; triethylamine In dichloromethane at 0 - 15℃; Darkness; Stage #2: diisopropylamine In dichloromethane; water; ethyl acetate | 92.8% |
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
Conditions | Yield |
---|---|
Stage #1: 7-amino-3-[2-(4-methyl-5-thiazolyl)vinyl]-3-cephem-4-carboxylic acid; (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate With triethylamine In tetrahydrofuran; water at 0 - 5℃; for 2.25 - 3.33333h; Stage #2: With potassium acetate In tetrahydrofuran; water; acetone at 20 - 25℃; | 89% |
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
B
2-Mercaptobenzothiazole
Conditions | Yield |
---|---|
Stage #1: 7-MPCA With triethylamine In dichloromethane for 0.5h; Stage #2: (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate In dichloromethane at 25 - 28℃; for 2h; Temperature; | A 89% B n/a |
ciprofloxacin
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
Conditions | Yield |
---|---|
With triethylamine In ethanol at 20 - 25℃; Schotten-Baumann reaction; | 88% |
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
cefditoren
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 5℃; for 4h; | 85% |
sulfadimethoxine
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
Conditions | Yield |
---|---|
With pyridine; triethylamine In ethanol; dichloromethane at 20℃; Inert atmosphere; | 84.6% |
(6R,7R)-7-amino-3-[(1Z)-2-(4-methyl-5-thiazolyl)vinyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
7-<(Z)-2-(2-Aminothiazol-4-yl)-2-methoxyiminoacetamido>-3(Z)-(4-methylthiazol-5-yl)vinyl-3-cephem-4-carboxylic acid sodium salt
Conditions | Yield |
---|---|
Stage #1: (6R,7R)-7-amino-3-[(1Z)-2-(4-methyl-5-thiazolyl)vinyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate With sulphurous acid; triethylamine In methanol; dichloromethane at 0 - 5℃; for 4h; Darkness; Stage #2: With (+/-)-2-n-ethylpentanoic acid sodium salt In water; acetone at 20 - 25℃; for 2h; Temperature; | 83.9% |
Stage #1: (6R,7R)-7-amino-3-[(1Z)-2-(4-methyl-5-thiazolyl)vinyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate With dmap; triethylamine In dichloromethane at 0 - 15℃; Darkness; Stage #2: With sodium isooctanoate In water; acetone | 82% |
sulfisoxazole
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
Conditions | Yield |
---|---|
With pyridine; triethylamine In ethanol; dichloromethane at 20℃; Inert atmosphere; | 83.1% |
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
(6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
cefpodoxime
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at -5 - 5℃; for 2h; | 82.86% |
With triethylamine In tetrahydrofuran at 0 - 5℃; for 2h; | 82.86% |
Stage #1: (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate; (6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid With triethylamine In methanol at 8 - 12℃; Stage #2: With sulfuric acid In methanol; water at 0 - 20℃; pH=2.4 - 2.5; Product distribution / selectivity; | |
With triethylamine In methanol; water at 15 - 20℃; | 81 mg |
(6R,7R)-7-amino-3-[(1Z)-2-(4-methyl-5-thiazolyl)vinyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
Conditions | Yield |
---|---|
Stage #1: (6R,7R)-7-amino-3-[(1Z)-2-(4-methyl-5-thiazolyl)vinyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate With triethylamine In dichloromethane at 0℃; Stage #2: With lithium tert-butoxide In dichloromethane; acetone for 1h; | 82.1% |
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
7-<(Z)-2-(2-Aminothiazol-4-yl)-2-methoxyiminoacetamido>-3(Z)-(4-methylthiazol-5-yl)vinyl-3-cephem-4-carboxylic acid sodium salt
Conditions | Yield |
---|---|
Stage #1: 7-amino-3-[2-(4-methyl-5-thiazolyl)vinyl]-3-cephem-4-carboxylic acid; (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate With triethylamine In tetrahydrofuran; water at 0 - 5℃; for 2.25 - 3.33333h; Stage #2: With sodium 2-ethylhexanoic acid In tetrahydrofuran; water; acetone at 20 - 25℃; | 75% |
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
sulfameter
Conditions | Yield |
---|---|
With pyridine; triethylamine In ethanol; dichloromethane at 20℃; Inert atmosphere; | 73.7% |
1-[((6R,7R)-7-amino-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl)methyl]-1-methylpyrrolidinium chloride hydrochloride
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
Conditions | Yield |
---|---|
Stage #1: 1-[((6R,7R)-7-amino-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl)methyl]-1-methylpyrrolidinium chloride hydrochloride; (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate With triethylamine In water; N,N-dimethyl-formamide at 20℃; for 3h; pH=7; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide Solvent; Reagent/catalyst; | 73% |
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
sarafloxacin
Conditions | Yield |
---|---|
With triethylamine In ethanol at 20 - 25℃; Schotten-Baumann reaction; | 72% |
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
sulfamethoxazole
Conditions | Yield |
---|---|
With pyridine; triethylamine In ethanol; dichloromethane at 20℃; Inert atmosphere; | 70.7% |
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
4-(2-aminoethyl)benzenesulfonamide
Conditions | Yield |
---|---|
With pyridine; triethylamine In ethanol; dichloromethane at 20℃; Inert atmosphere; | 65% |
sulfabenzamide
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
Conditions | Yield |
---|---|
With pyridine; triethylamine In ethanol; dichloromethane at 20℃; Inert atmosphere; | 65% |
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
1-amino-4-({[amino(imino)methyl]amino}sulfonyl)benzene
Conditions | Yield |
---|---|
With pyridine; triethylamine In ethanol; dichloromethane at 20℃; Inert atmosphere; | 64.7% |
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
sulfanilamide
Conditions | Yield |
---|---|
With triethylamine In ethanol at 20℃; Inert atmosphere; | 63.8% |
4-homosulfanilamide
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
Conditions | Yield |
---|---|
With pyridine; triethylamine In ethanol; dichloromethane at 20℃; Inert atmosphere; | 61.5% |
(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate
(6R-trans)-7-amino-3-<<<<4-(3-carboxy-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-quinolinyl)-1-piperazinyl>carbonyl>oxy>methyl>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid trifluoroacetic acid salt
<6R-<6α,7β-(Z)>>-7-<<(2-amino-4-thiazolyl)(methoxyimino)acetyl>amino>-3-<<<<4-(3-carboxy-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-quinolinyl)-1-piperazinyl>carbonyl>oxy>methyl>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid
Conditions | Yield |
---|---|
With potassium hydrogencarbonate In tetrahydrofuran; water Ambient temperature; | 59.8% |