Sodium Azide → (5R)-5-(azidomethyl)-3-(4-iodophenyl)-1,3-oxazolidin-2-one

HRID 747209Notes

Reaction equation

CS(O[CH2:6][C@@H:7]1[O:11][C:10](=[O:12])[N:9]([C:13]2[CH:18]=[CH:17][C:16]([I:19])=[CH:15][CH:14]=2)[CH2:8]1)(=O)=O.[N-:20]=[N+:21]=[N-:22].[Na+]>CC(N(C)C)=O.C(OCC)(=O)C>[N:20]([CH2:6][C@@H:7]1[O:11][C:10](=[O:12])[N:9]([C:13]2[CH:18]=[CH:17][C:16]([I:19])=[CH:15][CH:14]=2)[CH2:8]1)=[N+:21]=[N-:22]

Participants

Conditions

Temperature: 80 °C

Procedure

[(5R)-3-(4-Iodophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate (27 g, 68 mmol) was dissolved in dimethylacetamide (300 ml). Sodium azide (13.1 g, 202 mmol) was carefully added, and the solution was heated to 80° C. for 3 h. After cooling to room temperature, the mixture was diluted with ethyl acetate (500 ml), washed with water (2×), brine, and dried over sodium sulfate. Flash chromatography with 0-1% methanol in dichloromethane as eluent gave the desired product (19 g).

Workup

temperatureAfter cooling to room temperature
washwashed with water (2×), brine
dry with materialdried over sodium sulfate

Sources & evidence

ORD record: ord-d13ab42c2776418b80612fe5d2f297df
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07396847B2

Reaction notes

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