| Identification | Back Directory | [Name]
tert-butyl 5-oxo-L-prolinate | [CAS]
35418-16-7 | [Synonyms]
L-Pyr-Otbu
tert-Butyl L-PyroglutaMate
Tert butyl l-pyroglutamine
tert-butyl 5-oxo-L-prolinate
tert-Butyl L-Pyroglutamate >
5-Oxo-L-proline tert-butyl ester
Pyroglutamic acid tert-butyl ester
L-PyroglutaMic acid ter-butyl ester
L-PYROGLUTAMIC ACID TERT-BUTYL ESTER
2-Methyl-2-propanyl 5-oxo-L-prolinate
tert-butyl 5-oxo-L-prolinate USP/EP/BP
5-Oxo-L-proline 1,1-dimethylethyl ester
L-Proline,5-oxo-, 1,1-diMethylethyl ester
tert-Butyl (S)-2-Pyrrolidone-5-carboxylate
tert-Butyl (S)-5-oxopyrrolidine-2-carboxylate
tert-Butyl (S)-5-oxo-2-pyrrolidinecarboxylate
(S)-tert-Butyl 5-oxopyrrolidine-2-carboxylate
tert-butyl (2S)-5-oxopyrrolidine-2-carboxylate
5-Oxopyrrolidine-2α-carboxylic acid tert-butyl ester
(S)-5-Oxo-pyrrolidine-2-carboxylic acid tert-butyl ester
(2S)-5-Oxopyrrolidine-2-carboxylic acid tert-butyl ester | [EINECS(EC#)]
252-555-5 | [Molecular Formula]
C9H15NO3 | [MDL Number]
MFCD06659481 | [MOL File]
35418-16-7.mol | [Molecular Weight]
185.22 |
| Chemical Properties | Back Directory | [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 | [form ]
Powder | [pka]
14.65±0.40(Predicted) | [color ]
White | [BRN ]
3590226 |
| Hazard Information | Back Directory | [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 |
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