(S)-1-Benzyl 2-Methyl 4-Oxopyrrolidine-1,2-Dicarboxylate Chemical Properties

Boiling point:

422.1±45.0 °C(Predicted)

Density 

1.306±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform, Dichloromethane, Dimethylsulfoxide, Ethyl Acetate

form 

Oil

pka

-3.91±0.40(Predicted)

color 

Light Yellow

Safety Information

HazardClass 

IRRITANT

(S)-1-Benzyl 2-Methyl 4-Oxopyrrolidine-1,2-Dicarboxylate Usage And Synthesis

Chemical Properties

Light Yellow Oil

Uses

(S)-1-Benzyl 2-Methyl 4-Oxopyrrolidine-1,2-Dicarboxylate is used in the preparation of dipeptidyl peptidase IV inhibitors and (hydroxy)(carbamoyl)pyrimidinones as potent and orally bioavailable HIV integrase inhibitors.

Synthesis

General procedure for the synthesis of N-Cbz-4-oxo-L-proline methyl ester from (2S,4S)-N-CBZ-4-hydroxyproline methyl ester: Dess-Martin periodinane (3.0 g, 7.1 mmol) was added batchwise to a solution of compound (2S,4S)-N-CBZ-4-hydroxyproline methyl ester (1.0 g , 3.6 mmol) in a solution of dichloromethane (DCM, 20 mL). After addition, the reaction mixture was stirred at room temperature for 1.0 hour. After completion of the reaction, the mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate, v/v=5/1) to afford N-Cbz-4-oxo-L-proline methyl ester as a yellow oil (0.79 g, 79.5% yield). The structure of the compound was confirmed by the following spectral data: 1H NMR (400 MHz, CDCl3) δ (ppm): 7.47 (d, 2H, J=8.24 Hz), 7.38 (d, 2H, J=8.24 Hz), 7.24 (m, 1H), 5.09 (s, 2H), 4.18 (t, 1H), 3.68 (s, 3H). 3.38 (m, 1H), 3.32 (m, 1H), 2.21 (m, 1H), 1.96 (m, 1H).

References

[1] Patent: WO2014/82380, 2014, A1. Location in patent: Paragraph 00510; 00513
[2] Patent: EP2730572, 2014, A1. Location in patent: Paragraph 0706-0716
[3] Patent: EP2730572, 2015, B1. Location in patent: Paragraph 0706-0716
[4] Patent: WO2014/131315, 2014, A1. Location in patent: Page/Page column 176
[5] Patent: EP2730572, 2015, B1. Location in patent: Paragraph 0700; 0708

(S)-1-Benzyl 2-Methyl 4-Oxopyrrolidine-1,2-Dicarboxylate(16217-15-5)Related Product Information

• 1,2-Pyrrolidinedicarboxylic acid, 4-oxo-, 2-Methyl 1-(phenylMethyl) ester, (R)-