Cesium carbonate → HCID 68551508, compound

HRID 1446095Notes

Reaction equation

HRID 1446095 reaction equation
Br[C:2]1[N:3]([CH2:10][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][CH:23]([CH2:25][NH:26][C:27](=[O:29])[CH3:28])[O:22][C:21]3=[O:30])=[CH:16][C:15]=2[F:31])[CH2:12][OH:13])[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[F:31][C:15]1[CH:16]=[C:17]([N:20]2[CH2:24][CH:23]([CH2:25][NH:26][C:27](=[O:29])[CH3:28])[O:22][C:21]2=[O:30])[CH:18]=[CH:19][C:14]=1[CH:11]1[CH2:12][O:13][C:2]2=[N:6][C:5]([N+:7]([O-:9])=[O:8])=[CH:4][N:3]2[CH2:10]1

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 68550270HCID 68550270, compound

Product 1

HCID 68551508HCID 68551508, compoundYield 9.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of crude N-(3-{4-[2-(2-Bromo-4-nitro-imidazol-1-yl)-1-hydroxymethyl-ethyl]-3-fluoro-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide (9 mg, 0.018 mmol) in DMF (1 mL) was added Cs2CO3 (18 mg, 0.054 mmol) at rt, and stirred for 4 h at 50° C. The reaction mixture was cooled to rt, diluted with EtOAc, washed with brine & water. The organic layers were separated, dried (MgSO4) and concentrated. Prep TLC (5% MeOH/CH2Cl2) provided 690 μg of pale yellow solid. ESI MS m/z 420 (M+H+).

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. washwashed with brine & water
  3. customThe organic layers were separated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ffe44c42059f4614b18f8521bbedabe8
Source dataset
uspto-grants-2010_02
Patent number
US07666864B2

Reaction notes

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