Structure of 41360-32-1
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CAS No. : | 41360-32-1 |
Formula : | C8H8O5S |
M.W : | 216.21 |
SMILES Code : | O=C(O)C(C1=CC=CC=C1)S(=O)(O)=O |
MDL No. : | MFCD09952336 |
InChI Key : | USNMCXDGQQVYSW-UHFFFAOYSA-N |
Pubchem ID : | 413605 |
GHS Pictogram: | ![]() |
Signal Word: | Warning |
Hazard Statements: | H317-H319 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 14 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.12 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 5.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 48.52 |
TPSA ? Topological Polar Surface Area: Calculated from | 100.05 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from | -1.88 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by | 0.4 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from | 1.46 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from | 0.56 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by | -0.35 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions | 0.04 |
Log S (ESOL):? ESOL: Topological method implemented from | -1.55 |
Solubility | 6.07 mg/ml ; 0.0281 mol/l |
Class? Solubility class: Log S scale | Very soluble |
Log S (Ali)? Ali: Topological method implemented from | -2.07 |
Solubility | 1.85 mg/ml ; 0.00856 mol/l |
Class? Solubility class: Log S scale | Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by | -1.18 |
Solubility | 14.4 mg/ml ; 0.0665 mol/l |
Class? Solubility class: Log S scale | Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg | High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg | No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) | No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) | No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) | No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) | No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) | No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) | No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from | -7.33 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from | 0.0 |
Ghose? Ghose filter: implemented from | None |
Veber? Veber (GSK) filter: implemented from | 0.0 |
Egan? Egan (Pharmacia) filter: implemented from | 0.0 |
Muegge? Muegge (Bayer) filter: implemented from | 0.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat | 0.56 |
PAINS? Pan Assay Interference Structures: implemented from | 0.0 alert |
Brenk? Structural Alert: implemented from | 1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from | No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) | 2.58 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(1) Sulfonation reaction: The molten 200ml of 50percent oleum was transferred to a S03 generator, heated to 160°C, the generated S03 gas is passed into an absorption bottle containing 500 ml of 1,2-dichloroethane to generate white smoke in the absorption bottle, after the disappearance of the white smoke, the flow of S03 was stopped to prepare 200ml 1,2-dichloroethane S03 solution (wherein the number of moles of S03 is 1.84mmol); Under ice bath, 158 ml (1.84 mol) of 1,4-dioxane were added dropwise to the above solution, 152 g of phenylacetic acid were added in portions, stirred upto42 ~ 45 ° C and the reaction for 8 ~ 10h; (2) Quaternization : The reaction solution obtained in step (1) was poured into 600 ml of deionized water under an ice bath , stirred for 30min, making it layered, the organic phase was separated and washed 3 times or more with 0 ~ 5 ° C of deionized water, then sodium hydroxide at 0 ° C under ice bath, to adjust the pH value of 8 ~ 8.5, concentrated under reduced pressure to give crude styrene sulfonate disodium salt, and then 80percent ethanol was recrystallized, filtered , and dried to give sodium phenylacetate; where in, The method for the recrystallization of the alcohol washing is as follows: Alcohol solution with a concentration of 75 to 80percent as alcohol lotion, first 10~30min rapid stirring at a stirring rate than 500r / min, and then stir at a speed of 200 ~ 300r / min for 40 ~ 60min, finally, stirring at a rate of 30~50r / min for 20~30min to complete the recrystallization; (3) Ion exchange: Sodium phenylacetate obtained in step formulated as an aqueous solution of sodium phenylacetate of concentration 4 to 8percent , then 2 to 4 batches were added to the 732 cation exchange resin exchange column for exchange treatment, each batch of static exchange for 15 ~ 20min, collected exchange fluid of pH less than 7, resulting exchange fluid is enriched, again added to the exchange column, static exchange for 15 ~ 20min, collected exchange fluid of pH less than 5, finally, the exchange column is washed with deionized water, the effluent was collected, the exchange solution having a pH of less than 5 and the effluent were combined, concentrated under reduced pressure, and dried to obtain racemic a-sulfophenylacetic acid with water content less than 1 crystal water; Wherein, the drying method is: First dried in a vacuum oven in 0.05 ~ 0.08MPa,at 50 ~ 60 ° C for 3 ~ 5h, then placed in P2O5 desiccator and dried to save; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91.83% | With bis(trichloromethyl) carbonate; N,N-dimethyl-formamide; In 1,2-dichloro-ethane; at 5 - 20℃; for 1h; | A solution of D (-) - sulfophenylacetyl chloride in dichloroethane was prepared in the same manner as in Example 1 (1) except that the amount of BTC / C2H4Cl2 solution and solvent dichloroethane was used, that of BTC / C2H4Cl2 solution Dropping temperature, reaction time, the experimental results shown in Table 1 |
81% | With thionyl chloride; N-ethyl-N,N-diisopropylamine; In diethyl ether; at -2 - 25℃; for 1.5h; | (1) 52.4 g of alpha-<strong>[41360-32-1]sulfophenylacetic acid</strong> was stirred and dissolved in 100 mL of diethyl ether.115 mL of thionyl chloride was added dropwise at -2 °C.2.0 ml of N,N-diisopropylethylamine was added dropwise.The reaction was then stirred at a temperature of 25 ° C for 1.5 hours.After the reaction is completed, the mixture is distilled to dryness under reduced pressure.The residue after distillation was washed twice with diethyl ether.Then, it was distilled to dryness under reduced pressure to obtain 58.1 g of alpha-sulfophenylacetyl chloride.Yield 81.0percent; |
A solution of Compound 6 (238 mg, 1.1 mmol) in methylene chloride (10 ml) was cooled to 0° C. Diisopropylethylamine (480 mul, 2.75 mmol) followed by trimethylchlorosilane (422 mul, 3.3 mmol) were added, and then stirred at room temperature for 2 hours. After the reaction mixture was cooled to ?30° C., thionyl chloride (96 mul, 1.32 mmol) was added thereto, and then stirred at 0° C. for 1 hour to form a solution of the acid chloride. Meanwhile, Compound 2 (1.07 g, 1.0 mmol) was dissolved in methylene chloride (10 ml), and then cooled to ?60° C. Subsequently, tributylamine (951 mul, 4.0 mmol) was added thereto. To the resulting mixed solution, the above-described solution of the acid chloride was added dropwise over 30 minutes. After stirring at 0° C. for 1 hour, 0.5 mol/L hydrochloric acid was added to the reaction mixture, followed by extraction with methylene chloride. The organic layer was washed with 0.2 mol/L hydrochloric acid, aqueous sodium hydrogen sulfite solution, then saturated brine, and then dried with anhydrous magnesium sulfate. After removing the insoluble material through filtration, the filtrate was concentrated in vacuo, and then dried under reduced pressure to yield Compound 7 as a brown foam solid. |
With thionyl chloride; In diethyl ether; at 20℃; for 2h; | Under stirring at room temperature, to the alpha-<strong>[41360-32-1]sulfophenylacetic acid</strong> obtained in the step (3), 80 ml of diethyl ether and 176ml thionyl chloride, stirred at room temperature for 2h until uniform, 0.4ml catalyst DMF was added, heated to 42 ~ 43.5 ° C, stirred to carry out chlorosulfonylation reaction for 3.5 ~ 4h, the ether and excess thionyl chloride was evaporated under reduced pressure; (5) Sulfophenylacetyl chloride extraction: To the reaction mixture obtained in step (4), 360 ml of diethyl ether and n-hexane mixed in a volume ratio of 1: 1 were added in three portions, Sulfo phenylacetyl chloride crude was stirred, concentrated under reduced pressure, cooled and crystallized, filtered, evaporated to dryness , to give yellowish Sulfo phenylacetyl chloride; Where in, The cooling crystallization method is: First naturally cooled to room temperature, and then cooled to 0 ~ 5 ° C at a cooling rate of 5 ~ 10 ° C / min, the temperature was maintained for and then cooled to -15 ~ -20 ° C at a cooling rate of 3 ~ 5 ° C / min, the temperature was maintained for 20 ~ 30min, and finally cooled to -40 at a cooling rate of 1 ~ 3 ° C / min ° C, constant temperature to maintain for 30 ~ 60min; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
When trichloroethyl 7beta-amino-6alphaH-8-oxo-4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid is acylated with one of the following carboxylic acids:...cyanomethylsulfinylacetic acidcyanomethylsulfonylacetic acidalpha-carboxy-2-thienylacetic acidalpha-carboxy-3-thienylacetic acidalpha-sulphophenylacetic acid3-thienylacetic acid | ||
When trichloroethyl 7beta-amino-6alphaH-8-oxo-4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid is acylated with one of the following carboxylic acids:...cyanomethylsulfinylacetic acidcyanomethylsulfonylacetic acidalpha-carboxy-2-thienylacetic acidalpha-carboxy-3-thienylacetic acidalpha-sulphophenylacetic acid3-thienylacetic acid1-tetrazolylacetic acid | ||
When trichloroethyl 7beta-amino-6alphaH-8-oxo-4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid is acylated with one of the following carboxylic acids:...cyanomethylsulfinylacetic acidcyanomethylsulfonylacetic acidalpha-carboxy-2-thienylacetic acidalpha-carboxy-3-thienylacetic acidalpha-sulphophenylacetic acid3-thienylacetic acid1-tetrazoylacetic acid |
Tags: 41360-32-1 synthesis path| 41360-32-1 SDS| 41360-32-1 COA| 41360-32-1 purity| 41360-32-1 application| 41360-32-1 NMR| 41360-32-1 COA| 41360-32-1 structure
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