Water → (5R)-3-[3-Fluoro-4-(4-methyl-1H-imidazol-1-yl)phenyl]-5-(azidomethyl)oxazolidin-2-one

HRID 1268987Notes

Reaction equation

[N-:1]=[N+:2]=[N-:3].[Na+].CS(O[CH2:10][C@@H:11]1[O:15][C:14](=[O:16])[N:13]([C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24]3)=[C:19]([F:29])[CH:18]=2)[CH2:12]1)(=O)=O.C(OCC)(=O)C.O>CN(C=O)C.C1OCCOCCOCCOCCOCCOC1>[N:1]([CH2:10][C@@H:11]1[O:15][C:14](=[O:16])[N:13]([C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24]3)=[C:19]([F:29])[CH:18]=2)[CH2:12]1)=[N+:2]=[N-:3]

Participants

Conditions

Temperature: 90 °C

Procedure

Sodium azide (0.596 g, 9.08 mmol) and 18-crown-6 (0.025 g, 0.095 mmol) were added to a solution of (5R)-3-[3-fluoro-4-(4-methyl-1H-imidazol-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-ylmethyl methanesulfonate (WO 01/81350) (3.161 g, 8.56 mmol) in DMF (8.5 ml). The reaction mixture was heated to 90° C. under an atmosphere of nitrogen for 19 h. It was poured into a mixture of ethyl acetate and water and was extracted three times with ethyl acetate. The combined organic layers were washed once with brine, dried over sodium sulfate, filtered and the solvent was removed under vacuum to give 1.94 g of product as a white solid.

Workup

extractionwas extracted three times with ethyl acetate
washThe combined organic layers were washed once with brine
dry with materialdried over sodium sulfate
filtrationfiltered
customthe solvent was removed under vacuum

Sources & evidence

ORD record: ord-7b032021c5a948699dc670edcba416a4
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199143B2

Reaction notes

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