Side chain for meropenem Chemical Properties

Melting point:

117.0 to 121.0 °C

Boiling point:

555.8±50.0 °C(Predicted)

Density 

1.36±0.1 g/cm3(Predicted)

Flash point:

289.9 °C

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly), Water (Slightly)

form 

Solid

pka

9.94±0.40(Predicted)

color 

Pale Yellow to Light Yellow

Stability:

Hygroscopic

InChI

InChI=1S/C15H19N3O5S/c1-16(2)14(19)13-7-12(24)8-17(13)15(20)23-9-10-3-5-11(6-4-10)18(21)22/h3-6,12-13,24H,7-9H2,1-2H3/t12-,13-/m0/s1

InChIKey

VGLBNJWGUYQZHD-STQMWFEESA-N

SMILES

N1(C(OCC2=CC=C([N+]([O-])=O)C=C2)=O)C[C@@H](S)C[C@H]1C(N(C)C)=O

CAS DataBase Reference

96034-64-9(CAS DataBase Reference)

Safety Information

HS Code 

2933.99.8290

Side chain for meropenem Usage And Synthesis

Chemical Properties

White Crystalline Solid

Uses

Carbapenem antibiotic. Antibacterial

Uses

An intermediate used for the synthesis of Meropenem.

Uses

Side chain for meropenem

Synthesis

600 mL of N,N-dimethylformamide (DMF) was added to the reaction flask and the temperature of the reaction system was lowered to 0°C to 5°C. Subsequently, 179.5 g (0.55 mol) of (2S,4S)-1-carboxy-4-mercaptopyrrolidine (Formula VI) was added. Next, 66.8 g (0.66 mol) of diisopropylethylamine was added and the reaction mixture was stirred for 10 minutes. Then, 89.7 g (1.10 mol) of dimethylamine hydrochloride was added, and the reaction temperature was maintained between 0 °C and 5 °C, and the reaction continued to be stirred for 3 hours. Upon completion of the reaction, 500 mL of ice water was quickly added to the reaction mixture and stirred to precipitate a large amount of solid. The solid product was collected by filtration and the filter cake was washed with 200 mL of water. Finally, the product was dried under reduced pressure at 65 °C for 15 h to afford 179.4 g (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-(N,N-dimethylcarbamoyl)-4-mercapto-pyrrolidine (Formula VII) in 92.3% molar yield and 99.3% HPLC purity. The mass spectral data of compound VII were as follows: molecular formula C15H19N3O5S, molecular weight 353.4, [M+H]+: 354.6.

References

[1] Patent: CN105439932, 2016, A. Location in patent: Paragraph 0075; 0076; 0077
[2] Patent: CN105439933, 2016, A. Location in patent: Paragraph 0062; 0063; 0064

Side chain for meropenem(96034-64-9)Related Product Information

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