Sulbactam supplier | CasNO.68373-14-8

Name
Sulbactam
EINECS 269-878-2
CAS No. 68373-14-8
Article Data29
CAS DataBase
Density 1.62 g/cm³
Solubility Soluble in water at 18mg/ml
Melting Point 146-151oC
Formula C₈H₁₁NO₅S
Boiling Point 567.7 °C at 760 mmHg
Molecular Weight 233.245
Flash Point 297.1 °C
Transport Information
Appearance white to off-white crystalline powder
Safety 24/25
Risk Codes 22
Molecular Structure
Hazard Symbols Xn
Synonyms 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 3,3-dimethyl-7-oxo-, 4,4-dioxide, (2S-cis)-;Betamaze;CP 45899;Penicillanic acid 1,1-dioxide;Penicillanic acid S,S-dioxide;Penicillanic aciddioxide;Penicillanic acid sulfone;Sulbactam;Piperacillin Sodium and Sulbactam Sodium (1:8);Sulbactam Acid;
PSA 100.13000
LogP 0.22370

Synthetic route

: (2S,5R)-3,3-Dimethyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2-chloro-allyl ester

: 68373-14-8
sulbactum

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium 4-methylbenzenesulfinate In tetrahydrofuran; methanol for 1h; Ambient temperature;	99%

: 76646-91-8
6,6-dibromopenicillanic acid-1,1-dioxide

: 68373-14-8
sulbactum

Conditions

Conditions	Yield
With sulfuric acid; zinc In water at 12℃; for 2h; Temperature; Large scale;	96%
With hydrogenchloride; magnesium In dichloromethane; water at -5 - 3℃; for 0.5h; Reagent/catalyst; Solvent; Temperature;	93.1%
With tri-n-butyl-tin hydride In ethyl acetate at 20℃; for 2h; Temperature; Time; Inert atmosphere;	90.9%

: 69388-78-9
(2S,5R)-Benzyl 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate 4,4-Dioxide

: 68373-14-8
sulbactum

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethyl acetate for 1h; Ambient temperature;	96%

: 551-16-6, 1079-37-4, 3115-55-7, 21794-93-4, 145920-51-0
6-aminopenicillanic acid

: 68373-14-8
sulbactum

Conditions

Conditions	Yield
Stage #1: 6-aminopenicillanic acid With sulfuric acid; hypophosphorous acid; sodium nitrite In water; ethyl acetate at -10℃; for 1.5h; Stage #2: With sodium tungstate (VI) dihydrate; dihydrogen peroxide In water at -5℃; for 1h; Temperature;	94.9%

: 69388-84-7
sodium sulbactam

: 68373-14-8
sulbactum

Conditions

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In dichloromethane; water at 20℃; for 0.166667h; pH=6.9 - 7;	94.8%
With hydrogenchloride In water; ethyl acetate	87.2%
Multi-step reaction with 2 steps 1: 86 percent / hexamethylphosphoric acid triamide / 18 h / 55 °C 2: 99 percent / sodium p-toluenesulfinate tetrahydrate, Pd(PPh3)4 / methanol; tetrahydrofuran / 1 h / Ambient temperature View Scheme

: 76646-91-8
6,6-dibromopenicillanic acid-1,1-dioxide

: 7440-02-0
nickel

: 68373-14-8
sulbactum

Conditions

Conditions	Yield
With copper In dichloromethane; water; acetic acid; acetonitrile	84%

: 7439-96-5
manganese

: 810692-15-0
6-bromo-1,1-dioxopenicillanic acid

: 68373-14-8
sulbactum

Conditions

Conditions	Yield
With phosphoric acid; iron In acetic acid methyl ester; water	80%

: sodium salt of penicillanic acid

: 68373-14-8
sulbactum

Conditions

Conditions	Yield
With potassium permanganate; sodium chloride; sodium hydrogensulfite In water	78%

: 85871-31-4
(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl penicillanate 1,1-dioxide

: 68373-14-8
sulbactum

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water; acetone at 5 - 10℃; for 4h; pH 9;	65%

: 87-53-6
penicillanic acid

: 68373-14-8
sulbactum

Conditions

Conditions	Yield
With hydrogenchloride; sodium hydroxide; potassium permanganate; sodium hydrogensulfite In water; acetic acid; ethyl acetate	26%
With potassium permanganate; phosphoric acid; sodium hydroxide In water at 0 - 5℃; for 2h; pH=7.5; Temperature; pH-value;	49.5 g

: 76646-91-8
6,6-dibromopenicillanic acid-1,1-dioxide

A: 68373-14-8
sulbactum

B: 75527-87-6
6β-bromopenicillanic acid 1,1-dioxide

C: 75527-88-7
(2S,5R,6S)-6β-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,S,S-dioxide

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal under 2250.2 - 3750.3 Torr; Product distribution; Ambient temperature; pH 7.0 - 8.0;

...Expand

: 24158-88-1
6,6-dibromopenicillanic acid

: 68373-14-8
sulbactum

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: KMnO4; phosphoric acid / CH2Cl2; H2O / 0.83 h / -5 °C 2: Mg; aq.HCl / ethyl acetate; H2O / 10 h / 20 °C / pH 3.5 View Scheme
Multi-step reaction with 2 steps 1: 67 percent / KMnO4, NaOH, H3PO4 / CH2Cl2; H2O / -5 °C 2: 60.4 percent / NaOH, Zn / acetonitrile; H2O / 0 - 10 °C / 1) pH 5.2 2) pH 3.5-4 (by addition of 4M HCl), 30 min View Scheme
Multi-step reaction with 3 steps 1: Sodium orthovanadate; dihydrogen peroxide / dichloromethane; water / 2.5 h / 5 - 10 °C 2: potassium permanganate; ammonium acetate / dichloromethane; water / 2 h / 5 - 15 °C 3: magnesium; sulfuric acid / water; ethyl acetate / 1.75 h / 0 - 5 °C / pH 3.8 - 4 View Scheme
Multi-step reaction with 2 steps 1: sodium hydroxide; water; potassium permanganate; phosphoric acid / 0 - 5 °C 2: zinc / water / 1.5 h / 0 °C / pH Ca. 3.5 View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydroxide / water; ethyl acetate / 0.5 h / 5 °C / pH 7 1.2: 0.5 h / -5 °C 1.3: pH 1.23 2.1: hydrogenchloride; magnesium / water; ethyl acetate / 0.67 h / 0 °C / pH 3.5 - 4 View Scheme

: 115923-36-9
(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 6-diazopenicillanate

: 68373-14-8
sulbactum

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 85 percent / bromine / CH2Cl2 / 1 h / 0 - 5 °C 2: 72 percent / hydrogen, K2HPO4 / 5percent palladium on calcium carbonate / ethyl acetate; H2O / 2 h / 2068.6 Torr / Ambient temperature 3: 75 percent / 30percent hydrogen peroxide, sodium tungstate / acetone / 48 h / Ambient temperature 4: 65 percent / NaHCO3 / acetone; H2O / 4 h / 5 - 10 °C / pH 9 View Scheme
Multi-step reaction with 4 steps 1: 85 percent / bromine / CH2Cl2 / 1 h / 0 - 5 °C 2: 83.7 percent / m-chloroperbenzoic acid / CH2Cl2 / Ambient temperature 3: 80 percent / hydrogen, K2HPO4 / palladium on charcoal / ethyl acetate; H2O / 1 h / 2585.7 Torr / Ambient temperature 4: 65 percent / NaHCO3 / acetone; H2O / 4 h / 5 - 10 °C / pH 9 View Scheme

: 85871-33-6
(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl penicillanate

: 68373-14-8
sulbactum

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / 30percent hydrogen peroxide, sodium tungstate / acetone / 48 h / Ambient temperature 2: 65 percent / NaHCO3 / acetone; H2O / 4 h / 5 - 10 °C / pH 9 View Scheme

: 80715-30-6
6-aminopenicillanic acid (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl ester

: 68373-14-8
sulbactum

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 85 percent / sodium nitrile, 5percent aq. H2SO4 / H2O; CH2Cl2 / 1 h / 0 - 5 °C 2: 85 percent / bromine / CH2Cl2 / 1 h / 0 - 5 °C 3: 72 percent / hydrogen, K2HPO4 / 5percent palladium on calcium carbonate / ethyl acetate; H2O / 2 h / 2068.6 Torr / Ambient temperature 4: 75 percent / 30percent hydrogen peroxide, sodium tungstate / acetone / 48 h / Ambient temperature 5: 65 percent / NaHCO3 / acetone; H2O / 4 h / 5 - 10 °C / pH 9 View Scheme
Multi-step reaction with 5 steps 1: 85 percent / sodium nitrile, 5percent aq. H2SO4 / H2O; CH2Cl2 / 1 h / 0 - 5 °C 2: 85 percent / bromine / CH2Cl2 / 1 h / 0 - 5 °C 3: 83.7 percent / m-chloroperbenzoic acid / CH2Cl2 / Ambient temperature 4: 80 percent / hydrogen, K2HPO4 / palladium on charcoal / ethyl acetate; H2O / 1 h / 2585.7 Torr / Ambient temperature 5: 65 percent / NaHCO3 / acetone; H2O / 4 h / 5 - 10 °C / pH 9 View Scheme

Yield

Multi-step reaction with 5 steps
1: 85 percent / sodium nitrile, 5percent aq. H2SO4 / H2O; CH2Cl2 / 1 h / 0 - 5 °C
2: 85 percent / bromine / CH2Cl2 / 1 h / 0 - 5 °C
3: 72 percent / hydrogen, K2HPO4 / 5percent palladium on calcium carbonate / ethyl acetate; H2O / 2 h / 2068.6 Torr / Ambient temperature
4: 75 percent / 30percent hydrogen peroxide, sodium tungstate / acetone / 48 h / Ambient temperature
5: 65 percent / NaHCO3 / acetone; H2O / 4 h / 5 - 10 °C / pH 9
View Scheme

Multi-step reaction with 5 steps
1: 85 percent / sodium nitrile, 5percent aq. H2SO4 / H2O; CH2Cl2 / 1 h / 0 - 5 °C
2: 85 percent / bromine / CH2Cl2 / 1 h / 0 - 5 °C
3: 83.7 percent / m-chloroperbenzoic acid / CH2Cl2 / Ambient temperature
4: 80 percent / hydrogen, K2HPO4 / palladium on charcoal / ethyl acetate; H2O / 1 h / 2585.7 Torr / Ambient temperature
5: 65 percent / NaHCO3 / acetone; H2O / 4 h / 5 - 10 °C / pH 9
View Scheme

: 103453-04-9
(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 6,6-dibromopenicillanate

: 68373-14-8
sulbactum

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 72 percent / hydrogen, K2HPO4 / 5percent palladium on calcium carbonate / ethyl acetate; H2O / 2 h / 2068.6 Torr / Ambient temperature 2: 75 percent / 30percent hydrogen peroxide, sodium tungstate / acetone / 48 h / Ambient temperature 3: 65 percent / NaHCO3 / acetone; H2O / 4 h / 5 - 10 °C / pH 9 View Scheme
Multi-step reaction with 3 steps 1: 83.7 percent / m-chloroperbenzoic acid / CH2Cl2 / Ambient temperature 2: 80 percent / hydrogen, K2HPO4 / palladium on charcoal / ethyl acetate; H2O / 1 h / 2585.7 Torr / Ambient temperature 3: 65 percent / NaHCO3 / acetone; H2O / 4 h / 5 - 10 °C / pH 9 View Scheme

: 103453-09-4
(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 6,6-dibromopenicillanate 1,1-dioxide

: 68373-14-8
sulbactum

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / hydrogen, K2HPO4 / palladium on charcoal / ethyl acetate; H2O / 1 h / 2585.7 Torr / Ambient temperature 2: 65 percent / NaHCO3 / acetone; H2O / 4 h / 5 - 10 °C / pH 9 View Scheme

: 128971-79-9
(3S,4R)-4-<(2-Methyl-3-buten-2-yl)thio>-3-(trimethylsilyl)-2-azetidinone

: 68373-14-8
sulbactum

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 83 percent / i-Pr2NEt, N,N-(dimethylamino)pyridine / CH2Cl2 / 3 h / Ambient temperature 2: 1) O3, 2) Me2S / 1) CH2Cl2, -78 deg C, 2) 0 deg C, 15 min 3: 1) t-BuOK / 1) THF, t-BuOH, 0 deg C, 15 min, 2) 0 deg C, 40 h 4: 72 percent / Et3N, acetyl chloride / 20 h / 0 °C 5: 1) tetrabutylammonium fluoride, 2) ozone / 1) THF, -78 deg C, 1 h, 2) CH2Cl2, -78 deg C, 2 min 6: 91 percent / DBU / CH2Cl2 / 8 h 7: 93 percent / oxone, NaHCO3 / H2O; methanol / 18 h / Ambient temperature; pH 3 8: 96 percent / H2 / Pd/C / ethyl acetate / 1 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 8 steps
1: 83 percent / i-Pr2NEt, N,N-(dimethylamino)pyridine / CH2Cl2 / 3 h / Ambient temperature
2: 1) O3, 2) Me2S / 1) CH2Cl2, -78 deg C, 2) 0 deg C, 15 min
3: 1) t-BuOK / 1) THF, t-BuOH, 0 deg C, 15 min, 2) 0 deg C, 40 h
4: 72 percent / Et3N, acetyl chloride / 20 h / 0 °C
5: 1) tetrabutylammonium fluoride, 2) ozone / 1) THF, -78 deg C, 1 h, 2) CH2Cl2, -78 deg C, 2 min
6: 91 percent / DBU / CH2Cl2 / 8 h
7: 93 percent / oxone, NaHCO3 / H2O; methanol / 18 h / Ambient temperature; pH 3
8: 96 percent / H2 / Pd/C / ethyl acetate / 1 h / Ambient temperature
View Scheme

: 128971-80-2
(3S,4R)-1-(tert-Butyldimethylsilyl)-4-<(2-methyl-3-buten-2-yl)thio>-3-(trimethylsilyl)-2-azetidinone

: 68373-14-8
sulbactum

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 1) O3, 2) Me2S / 1) CH2Cl2, -78 deg C, 2) 0 deg C, 15 min 2: 1) t-BuOK / 1) THF, t-BuOH, 0 deg C, 15 min, 2) 0 deg C, 40 h 3: 72 percent / Et3N, acetyl chloride / 20 h / 0 °C 4: 1) tetrabutylammonium fluoride, 2) ozone / 1) THF, -78 deg C, 1 h, 2) CH2Cl2, -78 deg C, 2 min 5: 91 percent / DBU / CH2Cl2 / 8 h 6: 93 percent / oxone, NaHCO3 / H2O; methanol / 18 h / Ambient temperature; pH 3 7: 96 percent / H2 / Pd/C / ethyl acetate / 1 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 7 steps
1: 1) O3, 2) Me2S / 1) CH2Cl2, -78 deg C, 2) 0 deg C, 15 min
2: 1) t-BuOK / 1) THF, t-BuOH, 0 deg C, 15 min, 2) 0 deg C, 40 h
3: 72 percent / Et3N, acetyl chloride / 20 h / 0 °C
4: 1) tetrabutylammonium fluoride, 2) ozone / 1) THF, -78 deg C, 1 h, 2) CH2Cl2, -78 deg C, 2 min
5: 91 percent / DBU / CH2Cl2 / 8 h
6: 93 percent / oxone, NaHCO3 / H2O; methanol / 18 h / Ambient temperature; pH 3
7: 96 percent / H2 / Pd/C / ethyl acetate / 1 h / Ambient temperature
View Scheme

: 124831-31-8
(3S,4R)-1-(tert-Butyldimethylsilyl)-4-<(2-methyl-3-oxo-2-propyl)thio>-3-(trimethylsilyl)-2-azetidinone

: 68373-14-8
sulbactum

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 1) t-BuOK / 1) THF, t-BuOH, 0 deg C, 15 min, 2) 0 deg C, 40 h 2: 72 percent / Et3N, acetyl chloride / 20 h / 0 °C 3: 1) tetrabutylammonium fluoride, 2) ozone / 1) THF, -78 deg C, 1 h, 2) CH2Cl2, -78 deg C, 2 min 4: 91 percent / DBU / CH2Cl2 / 8 h 5: 93 percent / oxone, NaHCO3 / H2O; methanol / 18 h / Ambient temperature; pH 3 6: 96 percent / H2 / Pd/C / ethyl acetate / 1 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 6 steps
1: 1) t-BuOK / 1) THF, t-BuOH, 0 deg C, 15 min, 2) 0 deg C, 40 h
2: 72 percent / Et3N, acetyl chloride / 20 h / 0 °C
3: 1) tetrabutylammonium fluoride, 2) ozone / 1) THF, -78 deg C, 1 h, 2) CH2Cl2, -78 deg C, 2 min
4: 91 percent / DBU / CH2Cl2 / 8 h
5: 93 percent / oxone, NaHCO3 / H2O; methanol / 18 h / Ambient temperature; pH 3
6: 96 percent / H2 / Pd/C / ethyl acetate / 1 h / Ambient temperature
View Scheme

: 128971-81-3
(3S,4R)-4-<<4-(Benzyloxy)-3-hydroxy-2-methyl-4-nitro-2-butyl>thio>-1-(tert-butyldimethylsilyl)-3-(trimethylsilyl)-2-azetidinone

: 68373-14-8
sulbactum

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 72 percent / Et3N, acetyl chloride / 20 h / 0 °C 2: 1) tetrabutylammonium fluoride, 2) ozone / 1) THF, -78 deg C, 1 h, 2) CH2Cl2, -78 deg C, 2 min 3: 91 percent / DBU / CH2Cl2 / 8 h 4: 93 percent / oxone, NaHCO3 / H2O; methanol / 18 h / Ambient temperature; pH 3 5: 96 percent / H2 / Pd/C / ethyl acetate / 1 h / Ambient temperature View Scheme

: 124831-32-9
(3S,4R)-4-<<4-(Benzyloxy)-2-methyl-4-nitro-3(Z)-buten-2-yl>thio>-1-(tert-butyldimethylsilyl)-3-(trimethylsilyl)-2-azetidinone

: 68373-14-8
sulbactum

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 1) tetrabutylammonium fluoride, 2) ozone / 1) THF, -78 deg C, 1 h, 2) CH2Cl2, -78 deg C, 2 min 2: 91 percent / DBU / CH2Cl2 / 8 h 3: 93 percent / oxone, NaHCO3 / H2O; methanol / 18 h / Ambient temperature; pH 3 4: 96 percent / H2 / Pd/C / ethyl acetate / 1 h / Ambient temperature View Scheme

: 124831-33-0
(2R,5R)-Benzyl 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

: 68373-14-8
sulbactum

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 91 percent / DBU / CH2Cl2 / 8 h 2: 93 percent / oxone, NaHCO3 / H2O; methanol / 18 h / Ambient temperature; pH 3 3: 96 percent / H2 / Pd/C / ethyl acetate / 1 h / Ambient temperature View Scheme

: 62263-72-3
(2S,5R)-Benzyl 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

: 68373-14-8
sulbactum

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / oxone, NaHCO3 / H2O; methanol / 18 h / Ambient temperature; pH 3 2: 96 percent / H2 / Pd/C / ethyl acetate / 1 h / Ambient temperature View Scheme

: 76517-16-3
6-chloro-6-iodopenicillanic acid 1,1-dioxide

: 688-73-3
tri-n-butyl-tin hydride

: 68373-14-8
sulbactum

Conditions

Conditions	Yield
With chloro-trimethyl-silane; sodium hydrogencarbonate; triethylamine; 2,2'-azobis(isobutyronitrile) In ethyl acetate; benzene

: 76517-25-4
6-bromo-6-iodopenicillanic acid 1,1-dioxide

: 688-73-3
tri-n-butyl-tin hydride

: 68373-14-8
sulbactum

Conditions

Conditions	Yield
With chloro-trimethyl-silane; sodium hydrogencarbonate; triethylamine; 2,2'-azobis(isobutyronitrile) In hexane; ethyl acetate; benzene

: 76646-91-8
6,6-dibromopenicillanic acid-1,1-dioxide

: 551-16-6, 1079-37-4, 3115-55-7, 21794-93-4, 145920-51-0
6-aminopenicillanic acid

: 68373-14-8
sulbactum

Conditions

Conditions	Yield
palladium In ethyl acetate
palladium In ethyl acetate

: 7439-95-4
magnesium dihydride

: 2040-05-3
2,6 dichloroacetophenone

: 76646-91-8
6,6-dibromopenicillanic acid-1,1-dioxide

: 68373-14-8
sulbactum

Conditions

Conditions	Yield
With hydrogenchloride In hexane; water; ethyl acetate; acetone

...Expand

: 810692-15-0
6-bromo-1,1-dioxopenicillanic acid

: 68373-14-8
sulbactum

Conditions

Conditions	Yield
In acetic acid methyl ester; water

: 68373-14-8
sulbactum

: 69388-84-7
sodium sulbactam

Conditions

Conditions	Yield
With sodium isooctanoate In ethyl acetate	99.3%
With sodium 2-ethylhexanoic acid In water; isopropyl alcohol at 20 - 35℃; for 2.33333h;	95%
With sodium acetate; sodium hydrogencarbonate at 20 - 25℃; pH=5.5 - 6;
With sodium isooctanoate In methanol; water at 25℃; pH=4.5; Reagent/catalyst; Solvent; Temperature; pH-value;	542g

: 74-97-5
chlorobromomethane

: 68373-14-8
sulbactum

: 76247-40-0
chloromethyl penicillanate 1,1-dioxide

Conditions

Conditions	Yield
With pyridine at 20℃; for 3.5h; Darkness;	92.6%

: 16004-15-2
1-bromomethyl-4-iodobenzene

: 68373-14-8
sulbactum

: 4-iodobenzyl (2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]hept ane-2-carboxylate 4,4-dioxide

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide at 20℃; for 12h;	92%

: 628-21-7
1,4-Diiodobutane

: 68373-14-8
sulbactum

: C12H18INO5S

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 12h; Inert atmosphere;	86%

: 49715-04-0
chlorosulfuric acid chloromethyl ester

: 68373-14-8
sulbactum

: 76247-40-0
chloromethyl penicillanate 1,1-dioxide

Conditions

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane 1.) 20-22 deg C, 2.) 30 min;	80%

: 626-89-1
4-Methyl-1-pentanol

: 68373-14-8
sulbactum

: 4-methylpentyl (2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4,4-dioxide

Conditions

Conditions	Yield
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; for 16h;	78%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; Inert atmosphere;	74%

: 812-01-1
methyl chlorosulfate

: 68373-14-8
sulbactum

: 65039-72-7
2S,5R-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<2.2.0>-heptane-2 carboxylic acid methyl ester 4,4-dioxide

Conditions

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane 1.) 20-22 deg C, 2.) 30 min;	75%

: 68373-14-8
sulbactum

: 74-88-4
methyl iodide

: 65039-72-7
2S,5R-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<2.2.0>-heptane-2 carboxylic acid methyl ester 4,4-dioxide

Conditions

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 16h;	75%

: 68373-14-8
sulbactum

: 92975-18-3
[(chlorosulfonyl)oxy]methyl sulfurochloridate

: 81156-60-7
C17H22N2O10S2

Conditions

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane 1.) 20-22 deg C, 2.) 30 min;	73%

: 1-(1-bromoethyl)-4-bromomethyl-benzene

: 68373-14-8
sulbactum

: C17H20BrNO5S

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 3h;	70%

: 574-66-3
Benzophenone oxime

: 68373-14-8
sulbactum

: (2S,5R)-2-((((diphenylmethylene)amino)oxy)carbonyl)-3,3-dimethyl-4-thia-1-azabicyclo[3.2.0]heptan-7-one 4,4-dioxide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Schlenk technique; Inert atmosphere;	67%

: 62458-19-9
4,5-di(bromomethyl)-2-oxo-1,3-dioxole

: 68373-14-8
sulbactum

: 115946-67-3
(5-bromomethyl-2-oxo-1,3-dioxol-4-yl)methyl penicillanate 1,1-dioxide

Conditions

Conditions	Yield
With potassium hydrogencarbonate; sodium iodide In ethyl acetate; N,N-dimethyl-formamide for 8h; Ambient temperature;	61.5%

: 68373-14-8
sulbactum

: 88811-16-9
3-bromo-N-(triphenylmethyl)propanamine

: C30H32N2O5S

Conditions

Conditions	Yield
Stage #1: sulbactum With triethylamine In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 3-bromo-N-(triphenylmethyl)propanamine In N,N-dimethyl-formamide at 20℃; for 16h;	52%

: 68373-14-8
sulbactum

: 90906-61-9
α-chloroethyl chlorosulfate

: 76350-32-8
1-chloroethyl penicillanate 1,1-dioxide

Conditions

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane 1.) 20-22 deg C, 2.) 30 min;	47%

: potassium bicarbonate

: 80715-22-6
4-bromomethyl-1,3-dioxa-5-methylcyclopentene-2-one

: 68373-14-8
sulbactum

: 85871-31-4
(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl penicillanate 1,1-dioxide

Conditions

Conditions	Yield
With sodium chloride In N-methyl-acetamide; water; ethyl acetate	47%

...Expand

: 68373-14-8
sulbactum

: 3958-60-9
2-nitrophenylmethyl bromide

: 2-nitrobenzyl 3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0] heptane-2-carboxylate 4,4-dioxide

Conditions

Conditions	Yield
Stage #1: sulbactum With triethylamine In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 2-nitrophenylmethyl bromide In N,N-dimethyl-formamide at 20℃; for 16h;	46%

: 68373-14-8
sulbactum

: 18880-04-1
3,4-dichlorobenzyl bromide

: 3,4-dichlorobenzyl 3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0] heptane-2-carboxylate 4,4- dioxide

Conditions

Conditions	Yield
Stage #1: sulbactum With triethylamine In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 3,4-dichlorobenzyl bromide In N,N-dimethyl-formamide at 20℃; for 16h;	45%

: 841-77-0
diphenylmethylpiperazine

: 68373-14-8
sulbactum

: (2S)-3,3-dimethyl-2-(4'-benzhydrylpiperazine-1'-carbonyl)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane 4,4-dioxide

Conditions

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In N,N-dimethyl-formamide at 20℃;	40%

: 768-59-2
4-ethylbenzyl alcohol

: 68373-14-8
sulbactum

: 4-ethylbenzyl (2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4,4-dioxide

Conditions

Conditions	Yield
Stage #1: sulbactum With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: 4-ethylbenzyl alcohol In dichloromethane at 0 - 20℃; for 48h; Inert atmosphere;	27%

Sulbactam Specification

The Sulbactam , with cas registry number of 68373-14-8, is a kind of Peptide Synthesis/Antibiotics; Anti-Bacterial Agents; Anti-Infective Agents; Enzyme inhibitors. It is also called Sulbactam acid (base) . The IUPAC name is (2S,5R)-3,3-dimethyl-4,4,7-trioxo-4$l^{6}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid . And the systematic name is called (2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide . It should be stored at temperature of -20°C.

Physical properties of Sulbactam are: (1) ACD/LogP: -1.39 ; (2) # of Rule of 5 Violations: 0 ; (3) ACD/LogD (pH 5.5): -4.31 ; (4) ACD/LogD (pH 7.4): -5.11 ; (5) ACD/BCF (pH 5.5): 1 ; (6) ACD/BCF (pH 7.4): 1 ; (7) ACD/KOC (pH 5.5): 1 ; (8) ACD/KOC (pH 7.4): 1 ; (9) #H bond acceptors: 6 ; (10) #H bond donors: 1 ; (11) #Freely Rotating Bonds: 1 ; (12) Index of Refraction: 1.605 ; (13) Molar Refractivity: 49.42 cm³ ; (14) Molar Volume: 143.4 cm³ ; (15) Surface Tension: 71.3 dyne/cm ; (16) Enthalpy of Vaporization: 93.14 kJ/mol ; (17) Vapour Pressure: 2.26E-14 mmHg at 25°C.

Uses of Sulbactam : This compound is a irreversible inhibitor of beta-lactamase which is given in combination with beta-lactam antibiotics to inhibit beta-lactamase, an enzyme produced by bacteria that destroys the antibiotics.

You can still convert the following datas into molecular structure:
(1) SMILES:O=S2(=O)C([C@@H](N1C(=O)C[C@H]12)C(=O)O)(C)C;
(2) InChI:InChI=1/C8H11NO5S/c1-8(2)6(7(11)12)9-4(10)3-5(9)15(8,13)14/h5-6H,3H2,1-2H3,(H,11,12)/t5-,6+/m1/s1;
(3) InChIKey:FKENQMMABCRJMK-RITPCOANBJ

Product Name

Sulbactam

Synthetic route

Sulbactam Specification

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