Products Categories
CAS No.: | 1192500-31-4 |
---|---|
Name: | AvibactaM |
Article Data: | 8 |
Molecular Structure: | |
Formula: | C7H11N3O6S |
Molecular Weight: | 265.247 |
Synonyms: | AvibactaM;Sulfuric acid mono[(1R,2S,5R)-2-(aminocarbonyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl] ester |
Density: | 1.85 |
PSA: | 139.61000 |
LogP: | 0.58100 |
(2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicylco[3.2.1]octan-6-yl hydrogensulfate
Conditions | Yield |
---|---|
With chlorosulfonic acid In N,N-dimethyl-formamide at 30℃; for 48h; Reagent/catalyst; | 97% |
benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate
(2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicylco[3.2.1]octan-6-yl hydrogensulfate
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: potassium tert-butylate / dimethyl sulfoxide; tetrahydrofuran / 20 °C 1.2: -12 °C 2.1: ethyl acetate / Reflux 3.1: methanesulfonic acid / ethyl acetate / 42 °C 3.2: 52 °C 4.1: sodium tetrahydroborate; sulfuric acid; propionic acid / ethyl acetate / -20 °C 4.3: 40 - 45 °C 5.1: ammonia / methanol 6.1: N-ethyl-N,N-diisopropylamine; (fluorenylmethoxy)carbonyl chloride / chlorobenzene / 30 °C 7.1: hydrogen / 5% Pd-C / dichloromethane; N,N-dimethyl-formamide / 2250.23 Torr View Scheme | |
Multi-step reaction with 8 steps 1.1: potassium tert-butylate / dimethyl sulfoxide; tetrahydrofuran / 20 °C 1.2: -12 °C 2.1: ethyl acetate / Reflux 3.1: methanesulfonic acid / ethyl acetate / 42 °C 3.2: 52 °C 4.1: sodium tetrahydroborate; sulfuric acid; propionic acid / ethyl acetate / -20 °C 4.3: 40 - 45 °C 5.1: 1 h / 0 °C 5.2: 35 °C 6.1: ammonia / methanol / 20 °C 7.1: N-ethyl-N,N-diisopropylamine; (fluorenylmethoxy)carbonyl chloride / chlorobenzene / 30 °C 8.1: hydrogen / 5% Pd-C / dichloromethane; N,N-dimethyl-formamide / 2250.23 Torr View Scheme |
(1R,2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide
(2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicylco[3.2.1]octan-6-yl hydrogensulfate
Conditions | Yield |
---|---|
Stage #1: (1R,2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide With hydrogen; 5% Pd-C In dichloromethane; N,N-dimethyl-formamide under 2250.23 Torr; Stage #2: With sulfur trioxide-N,N-dimethylformamide complex; acetic acid In dichloromethane; N,N-dimethyl-formamide | |
With palladium 10% on activated carbon; hydrogen; sulfur trioxide trimethylamine complex; triethylamine In water; isopropyl alcohol for 5h; Large scale; Industrial scale; | |
With palladium 10% on activated carbon; water; hydrogen; sulfur trioxide trimethylamine complex; triethylamine In isopropyl alcohol |
(S)-ethyl N-tert-butoxycarbonylpyroglutamate
(2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicylco[3.2.1]octan-6-yl hydrogensulfate
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: potassium tert-butylate / dimethyl sulfoxide; tetrahydrofuran / 20 °C 1.2: -12 °C 2.1: ethyl acetate / Reflux 3.1: methanesulfonic acid / ethyl acetate / 42 °C 3.2: 52 °C 4.1: sodium tetrahydroborate; sulfuric acid; propionic acid / ethyl acetate / -20 °C 4.3: 40 - 45 °C 5.1: ammonia / methanol / 20 °C 6.1: N-ethyl-N,N-diisopropylamine; (fluorenylmethoxy)carbonyl chloride / chlorobenzene / 30 °C 7.1: hydrogen / 5% Pd-C / dichloromethane; N,N-dimethyl-formamide / 2250.23 Torr View Scheme |
(2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicylco[3.2.1]octan-6-yl hydrogensulfate
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: ethyl acetate / Reflux 2.1: methanesulfonic acid / ethyl acetate / 42 °C 2.2: 52 °C 3.1: sodium tetrahydroborate; sulfuric acid; propionic acid / ethyl acetate / -20 °C 3.3: 40 - 45 °C 4.1: potassium hydrogencarbonate / water; 2-methyltetrahydrofuran 4.2: 0 °C 5.1: water; lithium hydroxide monohydrate / acetone / -12 °C 5.2: 0 °C 5.3: -20 - 0 °C 6.1: hydrogen / 5% Pd-C / dichloromethane; N,N-dimethyl-formamide / 2250.23 Torr View Scheme | |
Multi-step reaction with 6 steps 1.1: ethyl acetate / Reflux 2.1: methanesulfonic acid / ethyl acetate / 42 °C 2.2: 52 °C 3.1: sodium tetrahydroborate; sulfuric acid; propionic acid / ethyl acetate / -20 °C 3.3: 40 - 45 °C 4.1: ammonia / methanol 5.1: N-ethyl-N,N-diisopropylamine; (fluorenylmethoxy)carbonyl chloride / chlorobenzene / 30 °C 6.1: hydrogen / 5% Pd-C / dichloromethane; N,N-dimethyl-formamide / 2250.23 Torr View Scheme | |
Multi-step reaction with 7 steps 1.1: ethyl acetate / Reflux 2.1: methanesulfonic acid / ethyl acetate / 42 °C 2.2: 52 °C 3.1: sodium tetrahydroborate; sulfuric acid; propionic acid / ethyl acetate / -20 °C 3.3: 40 - 45 °C 4.1: 1 h / 0 °C 4.2: 35 °C 5.1: 3-Methylpyridine / dichloromethane / 0 °C 6.1: ammonium carbamate / Novozyme 435 / dichloromethane; acetonitrile / 40 °C / Enzymatic reaction 7.1: hydrogen / 5% Pd-C / dichloromethane; N,N-dimethyl-formamide / 2250.23 Torr View Scheme | |
Multi-step reaction with 7 steps 1.1: ethyl acetate / Reflux 2.1: methanesulfonic acid / ethyl acetate / 42 °C 2.2: 52 °C 3.1: sodium tetrahydroborate; sulfuric acid; propionic acid / ethyl acetate / -20 °C 3.3: 40 - 45 °C 4.1: 1 h / 0 °C 4.2: 35 °C 5.1: ammonia / methanol / 20 °C 6.1: N-ethyl-N,N-diisopropylamine; (fluorenylmethoxy)carbonyl chloride / chlorobenzene / 30 °C 7.1: hydrogen / 5% Pd-C / dichloromethane; N,N-dimethyl-formamide / 2250.23 Torr View Scheme |
(2S)-5-(benzyloxyimino)-piperidine-2-carboxylic acid benzyl ester
(2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicylco[3.2.1]octan-6-yl hydrogensulfate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: sodium tetrahydroborate; sulfuric acid; propionic acid / ethyl acetate / -20 °C 1.3: 40 - 45 °C 2.1: potassium hydrogencarbonate / water; 2-methyltetrahydrofuran 2.2: 0 °C 3.1: water; lithium hydroxide monohydrate / acetone / -12 °C 3.2: 0 °C 3.3: -20 - 0 °C 4.1: hydrogen / 5% Pd-C / dichloromethane; N,N-dimethyl-formamide / 2250.23 Torr View Scheme | |
Multi-step reaction with 4 steps 1.1: sodium tetrahydroborate; sulfuric acid; propionic acid / ethyl acetate / -20 °C 1.3: 40 - 45 °C 2.1: ammonia / methanol 3.1: N-ethyl-N,N-diisopropylamine; (fluorenylmethoxy)carbonyl chloride / chlorobenzene / 30 °C 4.1: hydrogen / 5% Pd-C / dichloromethane; N,N-dimethyl-formamide / 2250.23 Torr View Scheme | |
Multi-step reaction with 5 steps 1.1: sodium tetrahydroborate; sulfuric acid; propionic acid / ethyl acetate / -20 °C 1.3: 40 - 45 °C 2.1: 1 h / 0 °C 2.2: 35 °C 3.1: 3-Methylpyridine / dichloromethane / 0 °C 4.1: ammonium carbamate / Novozyme 435 / dichloromethane; acetonitrile / 40 °C / Enzymatic reaction 5.1: hydrogen / 5% Pd-C / dichloromethane; N,N-dimethyl-formamide / 2250.23 Torr View Scheme | |
Multi-step reaction with 5 steps 1.1: sodium tetrahydroborate; sulfuric acid; propionic acid / ethyl acetate / -20 °C 1.3: 40 - 45 °C 2.1: 1 h / 0 °C 2.2: 35 °C 3.1: ammonia / methanol / 20 °C 4.1: N-ethyl-N,N-diisopropylamine; (fluorenylmethoxy)carbonyl chloride / chlorobenzene / 30 °C 5.1: hydrogen / 5% Pd-C / dichloromethane; N,N-dimethyl-formamide / 2250.23 Torr View Scheme |
(2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicylco[3.2.1]octan-6-yl hydrogensulfate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: methanol / 25 °C / Reflux 2.1: potassium hydrogencarbonate / water; 2-methyltetrahydrofuran 2.2: 0 °C 3.1: water; lithium hydroxide monohydrate / acetone / -12 °C 3.2: 0 °C 3.3: -20 - 0 °C 4.1: hydrogen / 5% Pd-C / dichloromethane; N,N-dimethyl-formamide / 2250.23 Torr View Scheme | |
Multi-step reaction with 4 steps 1: methanol / 25 °C / Reflux 2: ammonia / methanol 3: N-ethyl-N,N-diisopropylamine; (fluorenylmethoxy)carbonyl chloride / chlorobenzene / 30 °C 4: hydrogen / 5% Pd-C / dichloromethane; N,N-dimethyl-formamide / 2250.23 Torr View Scheme | |
Multi-step reaction with 5 steps 1.1: methanol / 25 °C / Reflux 2.1: 1 h / 0 °C 2.2: 35 °C 3.1: 3-Methylpyridine / dichloromethane / 0 °C 4.1: ammonium carbamate / Novozyme 435 / dichloromethane; acetonitrile / 40 °C / Enzymatic reaction 5.1: hydrogen / 5% Pd-C / dichloromethane; N,N-dimethyl-formamide / 2250.23 Torr View Scheme | |
Multi-step reaction with 5 steps 1.1: methanol / 25 °C / Reflux 2.1: 1 h / 0 °C 2.2: 35 °C 3.1: ammonia / methanol / 20 °C 4.1: N-ethyl-N,N-diisopropylamine; (fluorenylmethoxy)carbonyl chloride / chlorobenzene / 30 °C 5.1: hydrogen / 5% Pd-C / dichloromethane; N,N-dimethyl-formamide / 2250.23 Torr View Scheme |
benzyl (2S)-5-[(benzyloxy)imino]-2-{[(tert-butoxy)carbonyl]amino}-6-chlorohexanoate
(2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicylco[3.2.1]octan-6-yl hydrogensulfate
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: methanesulfonic acid / ethyl acetate / 42 °C 1.2: 52 °C 2.1: sodium tetrahydroborate; sulfuric acid; propionic acid / ethyl acetate / -20 °C 2.3: 40 - 45 °C 3.1: potassium hydrogencarbonate / water; 2-methyltetrahydrofuran 3.2: 0 °C 4.1: water; lithium hydroxide monohydrate / acetone / -12 °C 4.2: 0 °C 4.3: -20 - 0 °C 5.1: hydrogen / 5% Pd-C / dichloromethane; N,N-dimethyl-formamide / 2250.23 Torr View Scheme | |
Multi-step reaction with 5 steps 1.1: methanesulfonic acid / ethyl acetate / 42 °C 1.2: 52 °C 2.1: sodium tetrahydroborate; sulfuric acid; propionic acid / ethyl acetate / -20 °C 2.3: 40 - 45 °C 3.1: ammonia / methanol 4.1: N-ethyl-N,N-diisopropylamine; (fluorenylmethoxy)carbonyl chloride / chlorobenzene / 30 °C 5.1: hydrogen / 5% Pd-C / dichloromethane; N,N-dimethyl-formamide / 2250.23 Torr View Scheme | |
Multi-step reaction with 6 steps 1.1: methanesulfonic acid / ethyl acetate / 42 °C 1.2: 52 °C 2.1: sodium tetrahydroborate; sulfuric acid; propionic acid / ethyl acetate / -20 °C 2.3: 40 - 45 °C 3.1: 1 h / 0 °C 3.2: 35 °C 4.1: 3-Methylpyridine / dichloromethane / 0 °C 5.1: ammonium carbamate / Novozyme 435 / dichloromethane; acetonitrile / 40 °C / Enzymatic reaction 6.1: hydrogen / 5% Pd-C / dichloromethane; N,N-dimethyl-formamide / 2250.23 Torr View Scheme | |
Multi-step reaction with 6 steps 1.1: methanesulfonic acid / ethyl acetate / 42 °C 1.2: 52 °C 2.1: sodium tetrahydroborate; sulfuric acid; propionic acid / ethyl acetate / -20 °C 2.3: 40 - 45 °C 3.1: 1 h / 0 °C 3.2: 35 °C 4.1: ammonia / methanol / 20 °C 5.1: N-ethyl-N,N-diisopropylamine; (fluorenylmethoxy)carbonyl chloride / chlorobenzene / 30 °C 6.1: hydrogen / 5% Pd-C / dichloromethane; N,N-dimethyl-formamide / 2250.23 Torr View Scheme |
(2S,5R)-6-benzyloxy-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid methyl ester
(2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicylco[3.2.1]octan-6-yl hydrogensulfate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: ammonium carbamate / Novozyme 435 / acetonitrile / 40 °C / Enzymatic reaction 2: hydrogen / 5% Pd-C / dichloromethane; N,N-dimethyl-formamide / 2250.23 Torr View Scheme |
(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid benzyl ester
(2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicylco[3.2.1]octan-6-yl hydrogensulfate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: water; lithium hydroxide monohydrate / acetone / -12 °C 1.2: 0 °C 1.3: -20 - 0 °C 2.1: hydrogen / 5% Pd-C / dichloromethane; N,N-dimethyl-formamide / 2250.23 Torr View Scheme |