Triphosgene → (R)-METHYL 2-OXOOXAZOLIDINE-4-CARBOXYLATE

HRID 336334Notes

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]1

Participants

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-b370a75b7fbb4c9f90b04c286beeb7a9
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889671B2

Reaction notes

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