HuagongsheHuagongshe Chemistry Print Report · For research reference only
Carbon Dioxide → Methyl (4S)-2,5-dioxo-4-oxazolidinepropanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Carbon Dioxide | HCID 280 | — |
| Reactant | Phosgene | HCID 6371 | — |
| Reactant | N,N-Dimethylethylenediamine | HCID 66053 | — |
| Reactant | 4-Methyl-L-glutamate | HCID 440959 | — |
| Reactant | Methyl (4S)-2,5-dioxo-4-oxazolidinepropanoate | HCID 15725330 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Methyl (4S)-2,5-dioxo-4-oxazolidinepropanoate | HCID 15725330 | — |
| Product | Methyl-l-glutamate | HCID 21145003 | — |
Reaction Steps
Gamma-methyl-L-glutamate N-carboxy anhydride ("MLGlu-NCA") was prepared from gamma-methyl-L-glutamic acid ("MLGlu"; the gamma --COOH group protected as the ester --COOCH3) and phosgene (COCl2) in tetrahydrofuran (THF) using the phosgene method. MLGlu-NCA (MW 187, 1.496 g, 8.0 mmol) was suspended in 10 mL of anhydrous ethylene dichloride ("EDC", ClCH2CH2Cl). N,N-dimethylethylenediamine ("N,N-DMEDA," 13.6 mg, 154 micromol) was added with vigorous stirring. As carbon dioxide (CO2) evolved, the MLGlu-NCA went slowly into solution and after 2 hours of mixing, a clear solution of poly(methyl-L-glutamate (i.e., "PMLGlu") has formed.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05820850 |
| Source dataset | uspto-grants-1998_10 |
| ORD ID | ord-fff9b5b298d940e9bd1b5f26dec1d36f |
| Source note | uspto-grants-1998_10 |