Sodium Bicarbonate → HCID 178462328, compound

HRID 976339Notes

Reaction equation

HRID 976339 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[NH:9][N:8]=[N:7][C:6]=1[CH2:10][N:11]1[CH2:16][CH2:15][O:14][C@H:13]([O:17][C@@H:18]([C:20]2[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[C:22]([S:30][CH3:31])[CH:21]=2)[CH3:19])[C@@H:12]1[C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=1)[CH3:3].FC(F)(F)C(OO)=[O:42].C(=O)(O)[O-].[Na+]>FC(F)(F)C(O)=O>[CH3:1][N:2]([CH2:4][C:5]1[NH:9][N:8]=[N:7][C:6]=1[CH2:10][N:11]1[CH2:16][CH2:15][O:14][C@H:13]([O:17][C@@H:18]([C:20]2[CH:25]=[C:24]([C:26]([F:27])([F:28])[F:29])[CH:23]=[C:22]([S:30]([CH3:31])=[O:42])[CH:21]=2)[CH3:19])[C@@H:12]1[C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=1)[CH3:3]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 10290812Trifluoroperacetic acidHCID 178503240HCID 178503240, compound

Product 1

HCID 178462328HCID 178462328, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent2×

Conditions

Temperature
0 °C

Procedure

The thioether of Example 76 (155 mg, 0.28 mmol) was dissolved in trifluoroacetic acid (800 μl) cooled to 0° C. and treated with a 2.0M solution of trifluoroperacetic acid in trifluoroacetic acid (153 μl, 0.308 mmol), with stirring for 30 minutes. The reaction mixture was poured into 0.5M sodium bicarbonate solution (50 ml), extracted with dichloromethane (3×15 ml), dried (MgSO4) and concentrated in vacuo. The resulting crude solid (200 mg) was purified by flash silica gel chromatography in 8% methanol:dichioromethane to yield the title compound as unresolved stereoisomers as a white foam (81 mg, 51%). 1H NMR (360 MHz, CDCl3) δ 1.44 and 1.46 (3H total, 2×d, J=6.6 Hz), 2.24 (6H, s), 2.56 (1H, m), 2.59 and 2.62 (3H total, 2×s), 2.88 (1H, d, J=11.9 Hz), 3.23 and 3.26 (1H total, 2×d, J=13.9 Hz), 3.42-3.55 (3H, m), 3.62 (1H, br d, J=11.3 Hz), 3.75 and 3.79 (1H total, 2×d, J=14.4 Hz), 4.22 (1H, m), 4.32 and 4.35 (1H total, 2×d, J=2.7 Hz), 4.89 (1H, m), 6.85 (1/2H, s), 7.04-7.13 (3H, m), 7.24 (1/2H, s), 7.50 (2H, br s), 7.73 and 7.75 (1H total, 2×s); MS (ES+) m/z 570 (M+1, 100%).

Workup

  1. extractionextracted with dichloromethane (3×15 ml)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe resulting crude solid (200 mg) was purified by flash silica gel chromatography in 8% methanol

Sources & evidence

ORD record
ord-2c91d866b7fe4e48b18d1bddf53cbbb6
Source dataset
uspto-grants-1997_03
Patent number
US05612337

Reaction notes

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