Potassium Carbonate → (s)-Methyl 2-oxooxazolidine-4-carboxylate

HRID 54836

Reaction equation

HRID 54836 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][OH:8])[NH2:6].[C:10]([O-])([O-])=[O:11].[K+].[K+].ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>O.C1(C)C=CC=CC=1>[C:4]([C@@H:5]1[CH2:7][O:8][C:10](=[O:11])[NH:6]1)([O:3][CH3:2])=[O:9]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 94429TriphosgeneHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)

Product 1

HCID 385463(s)-Methyl 2-oxooxazolidine-4-carboxylateYield 88.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To (S)-serine methyl ester hydrochloride (20 g, 128.64 mmol) in water (230 ml) was added KHCO3 (14.16 g, 141.52 mmol) and K2CO3 (19.56 g, 141.52 mmol) at room temperature. It was then cooled by an ice bath and triphosgene (19.04 gm, 64.32 mmol) was added in toluene (192 ml) via an addition funnel over 25 minutes. The reaction mixture turned cloudy. After 2 h, reaction phases were separated and the aqueous layer was lyophilized to yield (S)-4-carbomethoxy-2-oxazolidinone as a white solid (16.5 g) in 88% yield.

Workup

  1. temperatureIt was then cooled by an ice bath
  2. customreaction phases
  3. customwere separated

Sources & evidence

ORD record
ord-5e16446cfae24e40a58886efbd0df072
Source dataset
uspto-grants-1997_04
Patent number
US05623087

Linked notes

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