Potassium Carbonate → HCID 59485897, compound

HRID 1972279Notes

Reaction equation

HRID 1972279 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]=[C:24]([F:26])[CH:23]=[C:22]([F:27])[CH:21]=1)(=O)=O.[CH3:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[N:36]=[N:37][NH:38][N:39]=2)=[CH:31][N:30]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([N:9]2[C@@H:8]([C:20]3[CH:21]=[C:22]([F:27])[CH:23]=[C:24]([F:26])[CH:25]=3)[C@H:7]([CH2:6][N:37]3[N:38]=[N:39][C:35]([C:32]4[CH:31]=[N:30][C:29]([CH3:28])=[CH:34][CH:33]=4)=[N:36]3)[O:11][C:10]2=[O:12])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 59485605HCID 59485605, compoundHCID 59485938HCID 59485938, compound

Product 1

HCID 59485897HCID 59485897, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

To a small reaction tube is placed ((4S,5R)-3-(4-chlorophenyl)-4-(3,5-difluorophenyl)-2-oxooxazolidin-5-yl)methyl methanesulfonate (50 mg, 0.12 mmol), ACN (1 mL), 2-methyl-5-(2H-tetrazol-5-yl)pyridine (39 mg, 0.24 mmol), and potassium carbonate (33 mg, 0.24 mmol). The tube is capped and the reaction is heated to 90° C. for 4 h. The reaction is then quenched with water (2 mL), and extracted with EtOAc, dried over MgSO4, filtered, and concentrated. The product is purified by flash chromatography (12 g Redisep, 0-10% MeOH/DCM) to give the title compound. 1H NMR (acetone-d6, 400 MHz) δ 9.18 (br s, 1H), 8.39 (d, J=8.1 Hz, 1H), 7.58 (br s, 1H), 7.47-7.44 (m, 2H), 7.29-7.23 (m, 2H), 7.02 (dddd, J=9.1, 9.1, 2.3, 2.3 Hz, 1H), 5.87 (d, J=5.0 Hz, 1H), 5.54 (dd, J=14.7, 5.8 Hz, 1H), 5.46 (dd, J=14.7, 4.0 Hz, 1H), 5.12 (ddd, J=5.7, 5.1, 4.0 Hz, 1H), 2.65 (s, 3H); HPLC-MS calculated C23H17ClF2N6O2 (M+H+) 483.1, found 483.0.

Workup

  1. customTo a small reaction tube is placed
  2. customThe tube is capped
  3. customThe reaction is then quenched with water (2 mL)
  4. extractionextracted with EtOAc
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product is purified by flash chromatography (12 g Redisep, 0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-08f1926f32514c5f9c2d1f2bf7ebbadc
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

Loading…