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D-P-METHYL SULFONE PHENYL ETHYL SERINATE

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D-P-METHYL SULFONE PHENYL ETHYL SERINATE manufacturers

D-P-METHYL SULFONE PHENYL ETHYL SERINATE Basic information
Product Name:D-P-METHYL SULFONE PHENYL ETHYL SERINATE
Synonyms:D-P-METHYL SULFONE PHENYL ETHYL SERINATE;Cuprum D-4-Methylsulfinophenylethylserinate;D-p-Methyl;D-p-Methyl-sulfino phenyl ethyl;D-p-Methyl sulfone phenyl ethyl serinate (d-PSE);(S)--Hydroxy-4-(methylsulfonyl)-D-phenylalanine Ethyl Ester;D-threo--Methylsulfonylphenylserine Ethyl Ester;(S)-beta-Hydroxy-4-(methylsulfonyl)-D-Phenylalanine ethyl ester
CAS:36983-12-7
MF:C12H17NO5S
MW:287.33
EINECS:1308068-626-2
Product Categories:Intermediates;Intermediates & Fine Chemicals;Pharmaceuticals;36983-12-7
Mol File:36983-12-7.mol
D-P-METHYL SULFONE PHENYL ETHYL SERINATE Structure
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
pka10.57±0.45(Predicted)
color White
Optical Rotation1.00°(C=0.01g/mL, MEOH, 589nm)
InChIInChI=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
InChIKeyCEEHCOWSYFANRT-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 Reference36983-12-7
Safety Information
MSDS Information
D-P-METHYL SULFONE PHENYL ETHYL SERINATE Usage And Synthesis
Chemical PropertiesWhite Solid
UsesFlorfenicol intermediate.
Synthesis
4-Methylsulphonyl benzaldehyde

5398-77-6

Glycine ethyl ester hydrochloride

623-33-6

3-(4-(METHYLSULFONYL)PHENYL)SERINE ETHYL ESTER

31925-27-6

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
D-P-METHYL SULFONE PHENYL ETHYL SERINATE Preparation Products And Raw materials
Raw materials4-Methylsulphonyl benzaldehyde-->Glycine ethyl ester hydrochloride-->Triethylamine-->Copper(II) sulfate pentahydrate
Tag:D-P-METHYL SULFONE PHENYL ETHYL SERINATE(36983-12-7) Related Product Information
Thiamphenicol DL-Glutamine D(-)-Asparagine monohydrate D(-)-Glutamic acid D-Methionine D-(-)-Asparagine monohydrate (+)-Dibenzoyl-D-tartaric acid (1S,2S)-(+)-2-AMINO-3-METHOXY-1-PHENYL-1-PROPANOL D-P-METHYL SULFONE PHENYL ETHYL SERINATE (1S,2S)-(+)-2-AMINO-1-[4-(METHYLTHIO)PHENYL]-1,3-PROPANEDIOL (S)-3-Fluoro-pyrrolidine hydrochloride (1S,2S)-(+)-2-Amino-1-phenyl-1,3-propanediol METHYL (R)-3-HYDROXY-3-PHENYLPROPANOATE DL-THREO-3-PHENYLSERINE BETA-HYDROXY-4-(METHYLSULFONYL)-PHENYLALANINE ETHYL ESTER (2R,3S)-3-PHENYLSERINE (+)-ETHYL (R)-3-HYDROXY-3-PHENYLPROPIONATE