| Identification | Back Directory | [Name]
5-OXO-PYRROLIDINE-2-CARBOXYLIC ACID METHYL ESTER | [CAS]
54571-66-3 | [Synonyms]
AKOS 90262
H-D-Pyr-OMe
METHYL DL-PYROGLUTAMATE
methyl 5-oxo-DL-prolinate
Proline, 5-oxo-, Methylester
(±)-5-Oxoproline methyl ester
5-Oxo-DL-proline methyl ester
DL-Pyroglutamic Acid Methyl Ester
Methyl 2-pyrrolidinone-5-carboxylate
METHYL 5-OXOPYRROLIDINE-2-CARBOXYLATE
Methyl DL-Pyroglutamate
Pyrrolidon-5-carbonsaeure-2-Methylester
DL-Methyl 5-oxopyrrolidine-2-carboxylate
Methyl5-oxopyrrolidine-2-carboxylate,95%
5-Oxo-2-pyrrolidinecarboxylic acid methyl ester
5-OXO-PYRROLIDINE-2-CARBOXYLIC ACID METHYL ESTER
(R)-5-Oxo-2-pyrrolidinecarboxylic acid methyl ester
(R)-5-Oxopyrrolidine-2β-carboxylic acid methyl ester
(2R)-5-Oxopyrrolidine-2-carboxylic acid methyl ester
(2R)-5-Oxopyrrolidine-2β-carboxylic acid methyl ester
rac-(R*)-5-Oxo-2-pyrrolidinecarboxylic acid methyl ester
H-D-Pyr-Ome/5-Oxo-Pyrrolidine-2-carboxylic acid methyl ester | [EINECS(EC#)]
259-233-3 | [Molecular Formula]
C6H9NO3 | [MDL Number]
MFCD03844651 | [MOL File]
54571-66-3.mol | [Molecular Weight]
143.14 |
| Chemical Properties | Back Directory | [Melting point ]
21-23℃ lit. | [Boiling point ]
133-135℃/1mm | [density ]
1.204 | [refractive index ]
1.4850 | [storage temp. ]
Inert atmosphere,Room Temperature | [form ]
Solid | [pka]
14.65±0.40(Predicted) | [color ]
Colorless to Brown | [InChI]
InChI=1S/C6H9NO3/c1-10-6(9)4-2-3-5(8)7-4/h4H,2-3H2,1H3,(H,7,8)/t4-/m0/s1 | [InChIKey]
HQGPKMSGXAUKHT-BYPYZUCNSA-N | [SMILES]
C(OC)(=O)[C@@H]1CCC(=O)N1 |
| Hazard Information | Back Directory | [Uses]
Methyl 5-Oxopyrrolidine-2-carboxylate, a purinoceptor antagonists in humans. | [Synthesis Reference(s)]
Journal of Heterocyclic Chemistry, 28, p. 1143, 1991 DOI: 10.1002/jhet.5570280452 | [Synthesis]
Sulfoxide chloride (6.60 mL, 90.6 mmol) was slowly added to a solution of 5-oxopyrrolidine-2-carboxylic acid (9.00 g, 69.7 mmol) in methanol (20 mL) at 0 °C. The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, the mixture was concentrated under vacuum. The residue was diluted with deionized water (100 mL) and extracted with ethyl acetate (100 mL). The organic phase was separated and washed sequentially with deionized water (20 mL) and saturated saline (50 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to give methyl 5-oxopyrrolidine-2-carboxylate (5.60 g, 58% yield) as a colorless liquid. The product did not need further purification and could be used directly in the subsequent reaction. Mass Spectrometry (ESI) m/z [M+H]+: 144.00, retention time: 1.33 min, relative abundance: 68.6%.1H NMR (400 MHz, DMSO-d6) δ 2.04-2.18 (m, 2H), 3.56-3.62 (m, 2H), 3.70 (s, 3H), 4.16-4.22 (m, 1H). 7.97 (s, 1H). | [References]
[1] Journal of Heterocyclic Chemistry, 1991, vol. 28, # 4, p. 1143 - 1146
[2] Synthesis (Germany), 2016, vol. 48, # 14, p. 2226 - 2244
[3] Journal of the American Chemical Society, 1987, vol. 109, # 25, p. 7925 - 7926
[4] Chemistry - A European Journal, 2005, vol. 11, # 8, p. 2577 - 2590
[5] Patent: EP2098526, 2009, A1. Location in patent: Page/Page column 13 |
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