7 β - aMino - 3 - [4 - pyridyl - 2 - thiazole sulfur radical ] - 3 - cepheM - 4 - carboxylic acid ·2HCl Chemical Properties

storage temp. 

Inert atmosphere,Room Temperature

InChI

InChI=1/C16H14N4O3S3.2ClH/c1-19-4-2-8(3-5-19)9-6-25-16(18-9)26-10-7-24-14-11(17)13(21)20(14)12(10)15(22)23;;/h2-6,11,14H,7,17H2,1H3;2*1H/t11-,14-;;/s3

InChIKey

SCEMEDZWEIWQPU-WDCXMVFZNA-N

SMILES

C1[N+](C)=CC=C(C2=CSC(SC3CS[C@@]4([H])N(C(=O)[C@H]4N)C=3C(O)=O)=N2)C=1.[Cl-].[H]Cl |&1:14,19,r|

7 β - aMino - 3 - [4 - pyridyl - 2 - thiazole sulfur radical ] - 3 - cepheM - 4 - carboxylic acid ·2HCl Usage And Synthesis

Uses

4-[2-[[(6R,7R)-7-Amino-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]thio]-4-thiazolyl]-1-methyl-pyridinium Chloride Monohydrochloride is a useful chemical reagent.

Synthesis

To a glass round bottom flask was added 35 g (51.7 mmol) of 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 8-oxo-7-[(2-phenylacetyl)amino]-3-[[4-(4-pyridinyl)-2-thiazolyl]thio]-, (6R,7R)-diphenylmethyl ester, and 75 mL of methylene chloride, and the temperature of the reaction was controlled at 25°C. To this solution was added 48 g (258.5 mmol) of methyl p-toluenesulfonate, and the mixture was heated to reflux and maintained at reflux for 12 hours and subsequently cooled to room temperature. In another glass-lined reactor, 32.3 g (155.1 mmol) of phosphorus pentachloride and 75 mL of methylene chloride were added. This suspension was cooled to -5°C to 0°C and 12.3 g (155.1 mmol) of pyridine was added dropwise while maintaining the temperature at -5°C to 0°C. After addition, stirring was continued at the same temperature for 15 minutes. The solution in the round-bottomed flask was carefully added to a glass-lined reactor that had been cooled to -10°C to -5°C while maintaining the temperature in the range of -10°C to -5°C; the resulting mixture was stirred at the same temperature for 2 hours. Subsequently, 105 mL of isobutanol was slowly added over about 30 minutes while maintaining a temperature in the range of -5°C; the mixture was heated to 28°C to 30°C and reacted at this temperature for 3.5 hours. Upon completion of the reaction, the mixture was concentrated under vacuum to 1/3 of the original volume, diluted with 200 mL of acetone, and stirred at 25°C to 30°C for 1 hour. 70 mL of 32% hydrochloric acid was added, the temperature was maintained at 25°C to 30°C and the mixture was stirred overnight. The resulting suspension was filtered and the filter cake was washed with acetone (2 x 35mL). The wet solid was dried under vacuum at 40 °C overnight to give 18.4 g (38.4 mmol) of 4-[2-[[(6R,7R)-7-amino-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3- yl]thio]-4-thiazolyl]-1-methylpyridinium chloride hydrochloride (1:1:1) as a crystalline solid. Yield 74.3%.

References

[1] Patent: WO2016/128580, 2016, A1. Location in patent: Page/Page column 21

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