Dimethylformamide → HCID 59485703, compound

HRID 1972278Notes

Reaction equation

HRID 1972278 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]([Cl:19])=[CH:15][CH:14]=2)[C@H:8]1[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=1)(=O)=O.[C:28]1([C:34]2[NH:35][CH:36]=CN=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:45][N:46](C=O)C>>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([N:9]2[C@@H:8]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=3)[C@H:7]([CH2:6][N:46]3[CH:45]=[C:34]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:35]=[CH:36]3)[O:11][C:10]2=[O:12])=[CH:14][CH:15]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 695912-PhenylimidazoleHCID 59485584HCID 59485584, compound

Product 1

HCID 59485703HCID 59485703, compound

Conditions

Temperature
70 °C

Procedure

A small reaction tube fitted with a screw cap is charged with ((4S,5R)-3-(4-chlorophenyl)-4-(3-methoxyphenyl)-2-oxooxazolidin-5-yl)methyl methanesulfonate (50 mg, 0.12 mmol) and DMF (1 mL). Phenylimidazole (35 mg, 0.24 mmol) is added followed by cesium carbonate (39 mg, 0.12 mmol) and the mixture is heated to 70° C. overnight. The reaction is then cooled to room temperature, quenched with water and extracted with EtOAc. The combined organics are washed with water, dried over MgSO4, filtered, concentrated, and purified by preparative HPLC (C-18, 10-90% ACN/water (0.05% TFA)) to give the title compound. 1H NMR (acetone-d6, 400 MHz) δ 7.80-7.78 (m, 3H), 7.68 (d, J=1.2 Hz, 1H), 7.46-7.42 (m, 2H), 7.34-7.17 (m, 6H), 6.96-6.93 (m, 2H), 6.89 (ddd, J=8.2, 2.5, 0.8 Hz, 1H), 5.46 (d, J=5.2 Hz, 1H), 4.83 (ddd, J=6.0, 5.0, 5.0 Hz, 1H), 4.70-4.69 (m, 2H), 3.72 (s, 3H); HPLC-MS calculated C26H22ClN3O3 (M+H+) 460.1, found 460.1.

Workup

  1. customA small reaction tube fitted with a screw
  2. customcap
  3. temperatureThe reaction is then cooled to room temperature
  4. customquenched with water
  5. extractionextracted with EtOAc
  6. washThe combined organics are washed with water
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified by preparative HPLC (C-18, 10-90% ACN/water (0.05% TFA))

Sources & evidence

ORD record
ord-7e79544c2ed2476894cac78a2c37f42b
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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