tert-butyl 5-oxo-L-prolinate Chemical Properties

Melting point:

102.0 to 108.0 °C

Boiling point:

319.2±35.0 °C(Predicted)

Density 

1.099±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

pka

14.65±0.40(Predicted)

form 

Powder

color 

White

BRN 

3590226

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/38

Safety Statements 

26

WGK Germany 

3

HS Code 

29339900

tert-butyl 5-oxo-L-prolinate Usage And Synthesis

Uses

tert-Butyl (S)-2-pyrrolidone-5-carboxylate can be used:

• As a starting material/synthon in the synthesis of angiotensin-converting enzyme inhibitors.
• In the synthesis of phenanthroindolizidine alkaloids named (+)-tylophorine and antofine.
• As a starting material in the synthesis of radioligands [¹⁸F]IUR-1602 and [¹⁸F]IUR-1601, applicable for imaging of P2X7R, a therapeutic target for neuroinflammation.

Synthesis

[0492] L-Pyroglutamic acid (5.0 g, 38.73 mmol) was dissolved in tert-butyl acetate (65 mL, 0.48 mol) under nitrogen protection, followed by the slow addition of 70% aqueous perchloric acid (1.25 mL). The reaction mixture was placed in a 250 mL round bottom flask and stirred for 18 hours at room temperature. Upon completion of the reaction, the mixture was carefully poured into saturated aqueous sodium bicarbonate solution to neutralize the excess acid. The aqueous phase was extracted with ethyl acetate (200 mL × 2), and the organic phases were combined and dried over anhydrous sodium sulfate. The organic phase was concentrated under reduced pressure and the residue was recrystallized from a solvent mixture of hexane/ether (10:1). The resulting white solid was collected by filtration and dried to give the title compound (S)-tert-butyl 5-oxopyrrolidine-2-carboxylate S2 (5 g, 70% yield).

References

[1] Synthetic Communications, 2005, vol. 35, # 8, p. 1129 - 1134
[2] European Journal of Organic Chemistry, 2018, vol. 2018, # 4, p. 455 - 460
[3] Organic letters, 2002, vol. 4, # 7, p. 1139 - 1142
[4] Patent: WO2010/45580, 2010, A1. Location in patent: Page/Page column 90
[5] Journal of Medicinal Chemistry, 2012, vol. 55, # 3, p. 1368 - 1381

tert-butyl 5-oxo-L-prolinate(35418-16-7)Related Product Information

• TERT-BUTYL 5-BROMOISOINDOLINE-2-CARBOXYLATE
• tert-butyl 5-bromoindoline-1-carboxylate
• tert-Butyl 7-bromoheptanoate
• L-Lactide
• Ethyl L-pyroglutamate
• 3-Boc-6-oxa-3-aza-bicyclo[3.1.0]hexane
• tert-Butyl 5-iodopentylcarbamate
• tert-Butyl 9-aminononanoate
• Hexanoic acid, 6-bromo-, 1,1-dimethylethyl ester
• tert-butyl(7-oxoheptyl) carbamate
• 5-BROMOPENTANOIC ACID, T-BUTYL ESTER
• TERT-BUTYL 6-IODOHEXYLCARBAMATE
• Methyl L-prolinate hydrochloride
• H-PRO-HYP-OH
• H-SER-GLY-OH
• Ethyl L-serinate hydrochloride
• tert-Butyl 6-oxohexylcarbamate
• tert-Butyl 8-oxooctylcarbamate