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| | (-)-D-PYROGLUTAMIC ACID METHYL ESTER Basic information |
| Product Name: | (-)-D-PYROGLUTAMIC ACID METHYL ESTER | | Synonyms: | (R)-PYROGLUTAMIC ACID METHYL ESTER;(-)-D-PYROGLUTAMIC ACID METHYL ESTER;(D)-PYROGLUTAMIC ACID METHYL ESTER;METHYL (R)-2-PYRROLIDINE-5-CARBOXYLATE;D-PYR-OME;METHYL (R)-(+)-2-PYRROLIDONE-5-CARBOXYLATE;Methyl (R)-(-)-2-pyrrolidinone;Methyl D-pyroglutaMate | | CAS: | 64700-65-8 | | MF: | C6H9NO3 | | MW: | 143.14 | | EINECS: | | | Product Categories: | | | Mol File: | 64700-65-8.mol |  |
| | (-)-D-PYROGLUTAMIC ACID METHYL ESTER Chemical Properties |
| 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 |
| | (-)-D-PYROGLUTAMIC ACID METHYL ESTER Usage And Synthesis |
| 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 |
| | (-)-D-PYROGLUTAMIC ACID METHYL ESTER Preparation Products And Raw materials |
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