Boc-L-Pyroglutamic acid methyl ester Chemical Properties

Melting point:

68-72 °C 69-74 °C

Boiling point:

361.6±35.0 °C(Predicted)

Density 

1.209±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Soluble in dichloromethane.

pka

-4.28±0.40(Predicted)

form 

powder to crystal

color 

White to Almost white

optical activity

[α]22/D 32.0°, c = 0.5 in chloroform &_& [α]22/D -32°, c = 0.5% in chloroform

InChI

InChI=1S/C11H17NO5/c1-11(2,3)17-10(15)12-7(9(14)16-4)5-6-8(12)13/h7H,5-6H2,1-4H3/t7-/m0/s1

InChIKey

FNTAOUUEQHKLIU-ZETCQYMHSA-N

SMILES

N1(C(OC(C)(C)C)=O)C(=O)CC[C@H]1C(OC)=O

CAS DataBase Reference

108963-96-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,N

Risk Statements 

36-43-50

Safety Statements 

26-36/37-61

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

3

HazardClass 

9

HS Code 

29337900

Boc-L-Pyroglutamic acid methyl ester Usage And Synthesis

Chemical Properties

Light Yellow Solid

Uses

Methyl (S)-1-Boc-5-oxopyrrolidine-2-carboxylate in medicine, pharmacy, cosmetics, and industrial, artificial flavoring and fragrance agents

Synthesis

(1) Synthesis of (2S)-5-oxopyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (Compound 3): L-pyroglutamic acid (15.0 g) was suspended in methanol (60.0 mL), and thionyl chloride (27.6 g) was slowly added with stirring at a temperature lower than 30°C. The reaction was completed after 1 hour by HPLC. After 1 hr of reaction, HPLC monitoring showed completion of the reaction. The solvent was removed by distillation under reduced pressure and the residue was dissolved in ethyl acetate (200 mL). Triethylamine (13.5 g) was slowly added at a temperature below 30 °C, followed by filtration of the mixture. To the filtrate was added DMAP (1.5 g) in a single addition, followed by di-tert-butyl dicarbonate (Boc2O, 27.8 g) at a temperature below 30 °C. After HPLC monitoring showed the reaction to be complete, the mixture was cooled to 0 °C and 1N HCl (13.0 mL) was added and stirred at a temperature below 30 °C for 10 min. The organic layer was separated, washed with H2O (20.0 mL) and the solvent was evaporated under reduced pressure. To the resulting residue was added tert-butyl methyl ether (27.0 mL) and cooled to 0°C with stirring. The slowly precipitated crystals were filtered to give compound 3 (21.9 g, 77.3% yield).

References

[1] Patent: WO2010/9014, 2010, A2. Location in patent: Page/Page column 6
[2] Patent: CN106336371, 2017, A. Location in patent: Paragraph 0050; 0051

Boc-L-Pyroglutamic acid methyl ester(108963-96-8)Related Product Information

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