Ethyl L-pyroglutamate

Ethyl L-pyroglutamate Property

Melting point:

54-56 °C

alpha 

-3.5 º (c=5, water)

Boiling point:

176 °C12 mm Hg(lit.)

Density 

1.2483 (rough estimate)

refractive index 

1.4310 (estimate)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Low Melting Solid

pka

14.78±0.40(Predicted)

color 

White to cream

optical activity

[α]19/D +3.3°, c = 10 in ethanol

BRN 

82621

InChI

InChI=1S/C7H11NO3/c1-2-11-7(10)5-3-4-6(9)8-5/h5H,2-4H2,1H3,(H,8,9)/t5-/m0/s1

InChIKey

QYJOOVQLTTVTJY-YFKPBYRVSA-N

SMILES

C(OCC)(=O)[C@@H]1CCC(=O)N1

LogP

-1.390 (est)

CAS DataBase Reference

7149-65-7(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

F 

3-10

HS Code 

29339900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Ethyl L-pyroglutamate Chemical Properties,Usage,Production

Chemical Properties

White to cream low melting solid

Uses

(S)-(+)-5-Ethylcarboxyl-2-pyrrolidinone (cas# 7149-65-7) is a compound useful in organic synthesis.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

30.0 g (232 mmol) of L-pyroglutamic acid was suspended in 100 mL of anhydrous ethanol and 20 mL (274 mmol, 1.2 eq.) of SOCl2 was slowly added dropwise at 0 °C. After the dropwise addition, the reaction mixture was stirred at 0 °C for 15 h. The reaction mixture was then allowed to warm up naturally to room temperature, resulting in a clarified solution. After completion of the reaction, all volatile components were removed under reduced pressure. The residue was dissolved in 500 mL of ethyl acetate and treated sequentially with K2CO3 and MgSO4 with stirring, removing the desiccant by filtration after each treatment. The solution was filtered through a small amount of silica gel and concentrated under reduced pressure to give 36.0 g (230 mmol, 99% yield) of the target product, ethyl (S)-5-oxopyrrolidine-2-carboxylate, in the form of a yellowish viscous oil. 2.22-2.48 (m, 3H, H-3α, H-4), 2.07-2.22 (m, 1H, H-3β), 1.22 (t, 3H, J = 7.1 Hz, ester CH3).13C-NMR (75 MHz, CDCl3): δ (ppm) = 178.37 (lactam CO), 172.10 (ester CO), 61.58 ( ester CH2), 55.59 (CH), 29.33 (CH2, C-4), 24.77 (CH2, C-3), 14.11 (ester CH3).

References

[1] Angewandte Chemie - International Edition, 2010, vol. 49, # 39, p. 7111 - 7115
[2] Patent: US2011/34438, 2011, A1. Location in patent: Page/Page column 20
[3] Patent: CN107304179, 2017, A. Location in patent: Paragraph 0033-0034
[4] Chemical Communications, 2014, vol. 50, # 68, p. 9690 - 9692
[5] Organic and Biomolecular Chemistry, 2006, vol. 4, # 21, p. 3894 - 3897