Triphosgene → (R)-Methyl 2-oxooxazolidine-4-carboxylate
Reaction equation
Cl.[CH3:2][O:3][C:4](=[O:9])[C@@H:5]([CH2:7][OH:8])[NH2:6].Cl[C:11](Cl)([O:13]C(=O)OC(Cl)(Cl)Cl)Cl>O1CCCC1>[O:13]=[C:11]1[NH:6][C@@H:5]([C:4]([O:3][CH3:2])=[O:9])[CH2:7][O:8]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a suspension of D-serine methyl ester hydrochloride (25.0 g, 160.7 mmol) in tetrahydrofuran (150 mL), a solution of triphosgene (47.68 g, 160.7 mmol) in tetrahydrofuran (100 mL) was added at 0° C. and the mixture was stirred at 80° C. for 2 hours. The volatiles were evaporated under vacuum and the residue was subjected to flash column silica gel chromatography using 5% methanol in chloroform. Yield: 17.5 g (75%). 1H NMR (400 MHz, DMSO-d6) δ: 3.69 (s, 3H), 4.32-4.33 (m, 1H), 4.32-4.33 (m, 2H), 8.22 (s, 1H).
Workup
- customThe volatiles were evaporated under vacuum
Sources & evidence
- ORD record
- ord-e07c05f6f02b4751a0acad1fce403179
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09187495B2
Reaction notes
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