Diethyl L-malate Chemical Properties

alpha 

-10.18°

Boiling point:

253℃

Density 

1.13

refractive index 

1.4330 to 1.4370

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

12.35±0.20(Predicted)

form 

Oil

color 

Colourless

Specific Gravity

1.1280 (20/4℃)

Dielectric constant

9.5（20℃）

CAS DataBase Reference

691-84-9(CAS DataBase Reference)

Safety Information

HS Code 

29181990

Diethyl L-malate Usage And Synthesis

Uses

Diethyl L-(-)-Malate is a reagent in the stereoselective synthesis of crucigasterin A and antitumor activity of crucigasterin A, B, and D.

Definition

ChEBI: Diethyl L-malate is a 3-hydroxy carboxylic acid.

Synthesis

Step 1 (Synthesis of compound 34-2) (0217) L-malic acid (80 g, 600 mmol) was dissolved in anhydrous ethanol (500 mL) and thionyl chloride (100 mL, 1.5 mol) was added slowly and dropwise at 0 °C. The reaction mixture was stirred at 0 °C for 20 min, then warmed to room temperature and continued to stir overnight. Upon completion of the reaction, the solvent was removed by concentration under reduced pressure and the residue was extracted with ethyl acetate (1000 mL x 3). The organic phases were combined and washed sequentially with water (500 mL×2) and saturated sodium chloride solution (500 mL×2), and the organic layer was dried with anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel column chromatography (eluent system: petroleum ether/ethyl acetate = 20:1) to afford diethyl (S)-2-hydroxysuccinate (113 g, 99% yield). (0218) 1H NMR (400 MHz, CDCl3) δ: 4.47 (q, J = 4.8 Hz, 1H), 4.26 (dq, J = 2.4, 7.2 Hz, 2H), 4.16 (q, J = 7.2 Hz, 2H), 3.28 (d, J = 4.8 Hz, 1H), 2.72-2.89 (m, 2H), 1.20- 1.34 (m, 6H).

References

[1] Patent: US2017/197986, 2017, A1. Location in patent: Paragraph 0216; 0217; 0218
[2] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 9, p. 969 - 974
[3] Journal of Polymer Science, Part A: Polymer Chemistry, 2015, vol. 53, # 22, p. 2586 - 2597
[4] European Journal of Organic Chemistry, 2012, # 5, p. 995 - 1002
[5] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 18, p. 5192 - 5194

Diethyl L-malate(691-84-9)Related Product Information

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