Carbon Dioxide → Methyl (4S)-2,5-dioxo-4-oxazolidinepropanoate

HRID 399365Notes

Reaction equation

HRID 399365 reaction equation
CC(C(O)=O)C[C@@H](C(O)=O)N.C(Cl)(Cl)=O.[CH3:16][O:17][C:18]([CH2:20][CH2:21][C@@H:22]1[NH:28][C:26](=[O:27])[O:25][C:23]1=[O:24])=[O:19].CN(C)CCN.C(=O)=O>O1CCCC1.C(Cl)CCl>[CH3:16][O:17][C:18]([CH2:20][CH2:21][C@@H:22]1[NH:28][C:26](=[O:27])[O:25][C:23]1=[O:24])=[O:19].[CH3:26][NH:28][C@H:22]([C:23]([O-:25])=[O:24])[CH2:21][CH2:20][C:18]([O-:19])=[O:17]

Participants

9

Reactant 5

HCID 280Carbon DioxideHCID 6371Phosgene2×HCID 66053N,N-DimethylethylenediamineHCID 4409594-Methyl-L-glutamate2×HCID 15725330Methyl (4S)-2,5-dioxo-4-oxazolidinepropanoate2×

Product 2

HCID 15725330Methyl (4S)-2,5-dioxo-4-oxazolidinepropanoateHCID 21145003Methyl-l-glutamate

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  1. additionof mixing

Sources & evidence

ORD record
ord-fff9b5b298d940e9bd1b5f26dec1d36f
Source dataset
uspto-grants-1998_10
Patent number
US05820850

Reaction notes

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