| Identification | Back Directory | [Name]
(-)-D-PYROGLUTAMIC ACID METHYL ESTER | [CAS]
64700-65-8 | [Synonyms]
D-PYR-OME
Methyl D-pyroglutaMate
Methyl (R)-pyroglutamate
5-Oxo-D-proline methyl ester
Methyl D-Pyroglutamate,99%e.e.
Methyl (R)-(-)-2-pyrrolidinone
D-Proline, 5-oxo-, Methyl ester
(R)-PYROGLUTAMIC ACID METHYL ESTER
(D)-PYROGLUTAMIC ACID METHYL ESTER
(-)-D-PYROGLUTAMIC ACID METHYL ESTER
(-)-D-PYROGLUTAMIC ACID METHYL ESTER
METHYL (R)-2-PYRROLIDINE-5-CARBOXYLATE
(R)-Methyl 2-pyrrolidone-5-carboxylate
(R)-METHYL 5-OXOPYRROLIDINE-2-CARBOXYLATE
Methyl (R)-5-oxopyrrolidine-2-carboxylate
methyl (2R)-5-oxopyrrolidine-2-carboxylate
METHYL (R)-(+)-2-PYRROLIDONE-5-CARBOXYLATE
Methyl (R)-(-)-2-pyrrolidinone-5-carboxylate, 98% | [Molecular Formula]
C6H9NO3 | [MDL Number]
MFCD01318621 | [MOL File]
64700-65-8.mol | [Molecular Weight]
143.14 |
| Chemical Properties | Back Directory | [Boiling point ]
83℃/0.25mm | [density ]
1.226 | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Dichloromethane | [form ]
Oil | [pka]
14.65±0.40(Predicted) | [color ]
Clear | [Sensitive ]
Moisture Sensitive | [InChI]
InChI=1S/C6H9NO3/c1-10-6(9)4-2-3-5(8)7-4/h4H,2-3H2,1H3,(H,7,8)/t4-/m1/s1 | [InChIKey]
HQGPKMSGXAUKHT-SCSAIBSYSA-N | [SMILES]
C(OC)(=O)[C@H]1CCC(=O)N1 |
| Hazard Information | Back Directory | [Uses]
(R)-Methyl 5-Oxopyrrolidine-2-carboxylate, is a building block used in various chemical synthesis such as in preparation of phenylpropiolic acid derivatives as novel GPR40 agonists. | [Synthesis]
The general procedure for the synthesis of methyl (S)-(+)-2-pyrrolidone-5-carboxylate from methanol and DL-pyroglutamic acid was as follows: DL-pyroglutamic acid (2150 g, 16.65 mol) was dissolved in a solvent mixture of methanol (2.0 L) and chloroform (2.0 L), and methanesulfonic acid (80 g, 0.83 mol) was added. This mixture was transferred to a Soxhlet extraction apparatus fitted with 3? molecular sieves and the reaction was refluxed under mechanical stirring for 5 days. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure to afford methyl (S)-(+)-2-pyrrolidone-5-carboxylate as a yellow oil in 98% yield (16.3 mmol). The product could be used in the next reaction without further purification and its physicochemical properties were consistent with those reported in the literature.1H NMR (CDCl3, 400 MHz) δ ppm: 2.08-2.50 (m, 4H, CHCH2CH2), 3.77 (s, 3H, CH3), 4.29 (m, 1H, CH2CH2CH), 7.62 (br s, 1H, NH). NH). | [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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