D-P-METHYL SULFONE PHENYL ETHYL SERINATE Chemical Properties

Melting point:

135-137°C

Boiling point:

515.0±50.0 °C(Predicted)

Density 

1.309

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

solubility 

Chloroform

form 

Solid

pka

10.57±0.45(Predicted)

color 

White

optical activity

1.00°(C=0.01g/mL, MEOH, 589nm)

InChI

InChI=1/C12H17NO5S/c1-3-18-12(15)10(13)11(14)8-4-6-9(7-5-8)19(2,16)17/h4-7,10-11,14H,3,13H2,1-2H3/t10-,11+/s3

InChIKey

CEEHCOWSYFANRT-WQVXQJEGNA-N

SMILES

[C@@H](C1C=CC(S(=O)(=O)C)=CC=1)(O)[C@@H](N)C(=O)OCC |&1:0,12,r|

CAS DataBase Reference

36983-12-7

D-P-METHYL SULFONE PHENYL ETHYL SERINATE Usage And Synthesis

Chemical Properties

White Solid

Uses

Florfenicol intermediate.

Synthesis

GENERAL STEPS: 500 g (15.6 mol) of methanol was added to a 1000 ml three-necked flask. Under stirring conditions, 73.9 g (0.53 mol) of ethyl glycinate hydrochloride was added and the temperature was slowly raised to 50-55°C until the ethyl glycinate hydrochloride was completely dissolved. Subsequently, 67.5 g (0.27 mol) of copper sulfate pentahydrate was added to this solution and stirring was continued until complete dissolution and stirring was maintained at 50-55°C for 0.5 hr. Next, triethylamine was added dropwise to the reaction system and the pH was adjusted to 8.5-9.0. Then, 92 g (0.5 mol) of p-methylsulfonylbenzaldehyde was added, and the reaction temperature was maintained at 50-55 °C and the pH was maintained between 8.5-9.0 by adding triethylamine. During the reaction, the progress of the reaction was monitored by HPLC, and the reaction was judged to be complete when the percentage of peak area of p-methylsulfonylbenzaldehyde was less than 2%. At the end of the reaction, methanol was recovered by decompression distillation, and the temperature inside the reaction flask was controlled to be no more than 50 °C during the distillation process. After the recovery of methanol, 600 g of water was added to the reaction flask, and after sufficient stirring, 146.7 g of ethyl 3-(p-toluenesulfonylphenyl)serinate was obtained by centrifugation, with a moisture content of 10.0%, a purity of 97.2% and a yield of 92%.

References

[1] Patent: CN108373430, 2018, A. Location in patent: Paragraph 0017; 0040; 0045-0059

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