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Basic Information

Molecular Structure:
CAS No.:	68373-14-8
Name:	Sulbactam
Article Data:	29

Formula:	C₈H₁₁NO₅S
Molecular Weight:	233.245
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;
EINECS:	269-878-2
Density:	1.62 g/cm³
Melting Point:	146-151oC
Boiling Point:	567.7 °C at 760 mmHg
Flash Point:	297.1 °C
Solubility:	Soluble in water at 18mg/ml
Appearance:	white to off-white crystalline powder
Hazard Symbols:	Xn
Risk Codes:	22
Safety:	24/25
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

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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