(2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide
SALBACTAM ACID
CAS: 68373-14-8
Molecular Formula: C8H11NO5S
(2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide - Names and Identifiers
(2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide - Physico-chemical Properties
| Molecular Formula | C8H11NO5S |
| Molar Mass | 233.24 |
| Density | 1.62±0.1 g/cm3(Predicted) |
| Melting Point | 154-157℃ |
| Boling Point | 567.7±50.0 °C(Predicted) |
| Specific Rotation(α) | D20 +251° (c = 0.01 in pH 5.0 buffer) |
| Flash Point | 297.1°C |
| Water Solubility | Soluble in water at 18mg/ml |
| Solubility | H2O: ≥18mg/mL |
| Vapor Presure | 2.26E-14mmHg at 25°C |
| Appearance | lyophilized powder |
| Color | white to tan |
| Merck | 14,8889 |
| pKa | 2.62±0.40(Predicted) |
| Storage Condition | 2-8°C |
| Stability | Hygroscopic |
| Refractive Index | 1.605 |
| Physical and Chemical Properties | A white crystalline solid having a melting point of 148 to 151 ° C.; A melting point of 154 to 155 ° C. (decomposition) has also been reported. [Α] D 20 251 °(C = 0.01,Ph = 5 buffer solution). Soluble in water. Sulbactam Sodium: C8H10NNaO5S. [69388-84-7]. White or off-white crystalline powder, soluble in water. |
| Use | Β-lactamase inhibitors |
(2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 22 - Harmful if swallowed |
| Safety Description | 24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| HS Code | 29349990 |
(2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide - Upstream Downstream Industry
| Downstream Products | Sulbactam sodium |
(2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide - Reference Information
| biological activity | Sulbactam is a β-lactamase inhibitor with an IC50 of 0.8 μm. |
| Use | The β-lactamase inhibitor has a strong irreversible inhibitory effect on penicillinase and cephalosporinase. Its antibacterial activity is very weak, so it is rarely used alone, often used in combination with other beta-lactam antibiotics, there is a significant synergistic effect, the majority of resistant bacteria are effective. And cefoperazone compound preparation of Sulperzon (Sulperzon) for the treatment of infection of drug-resistant bacteria; And ampicillin compound preparation of ampicillin. A β-lactamase inhibitor used in the synthesis of sulbactam sodium |
| production method | Method 1:6.51g(41 mmol) of potassium permanganate is dissolved in ml of water and 4.95ml of glacial acetic acid, it was cooled to about 5 °c. A solution of about 4.58g(21 mmol) of sodium penicillate in 50RNL of water at 5 °c was added and stirred at 5 °c for 20min. The cooling bath was removed and solid sodium bisulfite was added until the color of the potassium permanganate disappeared and then filtered. A half volume of a saturated aqueous solution of sodium chloride was added to the filtrate to adjust the pH to 1.7. The acidic aqueous solution was extracted with ethyl acetate. The extract was dried and concentrated under reduced pressure to give 3.47g of sulbactam. The acidic aqueous solution after extraction was saturated with sodium chloride and extracted with ethyl acetate. The extract was dried and concentrated to obtain 0.28g of sulbactam. A total of 3.75g of sulbactam was obtained in a yield of 78%. Method 2: 6-APA was used as raw material. Sodium bromide and sulfuric acid are mixed (hydrobromic acid can also be used), and 67APA is added under stirring at 0 ° C., and after 6-APA is completely dissolved, an aqueous solution of sodium nitrite is added dropwise. After addition, the reaction was carried out at a temperature below 4 °c. The aqueous layer was separated and extracted twice with dichloromethane. The oil was extracted with the extract, Then washed with water. An equal amount of water was added and neutralized to neutrality. The aqueous solution containing 6-bromopenicillanic acid was separated and used directly in the next reaction. The potassium permanganate, water and glacial acetic acid were mixed, and the aqueous solution of 6-bromopicillanic acid obtained in the above reaction was added at 0 ° C. With stirring. The reaction was carried out below 5 °c for 1H. Sodium bisulfite was added to decolorize, chloroform was added, and the pH was adjusted to pH = 2 with sulfuric acid. The chloroform layer was separated and the aqueous layer was extracted with chloroform. The chloroform layers were combined, washed with water and dried. The chloroform was distilled off under reduced pressure, and the crystals were precipitated, collected by filtration, washed with chloroform, and dried to obtain 6-bromopenicillane sulfone acid. 6-bromopenicillane sulfone acid was mixed with water, adjusted to Neutral with sodium hydroxide, and 10% palladium-carbon and disodium hydrogen phosphate were added for hydrogenolysis. After filtration, the filtrate was added with ethyl acetate and adjusted to pH = 2 with sulfuric acid. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with water, dried and concentrated under reduced pressure to obtain yellowish crystals, which were washed with ethyl acetate and dried under vacuum to obtain sulbactam, which could be recrystallized from ethyl acetate-petroleum ether. Method 3: bromine, sulfuric acid and sodium nitrite were added to methylene chloride at 5 °c. 6-APA was then added in portions at 4-10 °c. After stirring at 5 °c, Sodium bisulfite solution was then added dropwise at 5-15 °c until the bromine color disappeared to form a pale yellow solution. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The organic layers were combined and washed with brine to give a solution of the dibromide in dichloromethane, which was used directly in the next reaction. Water was added to the above solution of dibromide in dichloromethane, and sodium hydroxide solution was added dropwise to Ph = 7.0. The aqueous layer was separated and the organic layer was extracted with water. The extract and the aqueous layer were combined, and potassium permanganate solution was added dropwise to the aqueous layer under stirring at -5 °c. Ethyl acetate was added and adjusted to pH = 1.23 with hydrochloric acid. To the resulting biphasic solution, sodium bisulfite solution was added dropwise below 10 °c and the pH was maintained at 1.25 to 1.35 with hydrochloric acid. The aqueous layer was separated after saturation with sodium chloride and extracted with ethyl acetate. The extract and the organic layer were combined, washed with brine, dried, and filtered to give an ethyl acetate solution containing the oxidized product, which was used directly in the next step. The above ethyl acetate solution, saturated sodium bicarbonate solution and 5% palladium-on-charcoal were hydrogenated at a hydrogen pressure of about 0.35MPa. Filter, cool to about 5 °c, and adjust the pH to 1.2 with hydrochloric acid. After saturated with sodium chloride, the aqueous layer was extracted with ethyl acetate, the extract and the organic layer were combined, dried and concentrated under reduced pressure to obtain the crude sulbactam, The yield was 57.5%. Method 4: sulbactam was prepared by using penicillin G as raw material, using M-chloroperoxybenzoic acid to oxidize sulphone into sulfone, and then hydrogenolysis. |
Last Update：2024-04-09 02:00:10
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Downstream Products for (2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide