Acetaldehyde → HCID 178432463, compound

HRID 705354Notes

Reaction equation

HRID 705354 reaction equation
[CH:1]1([C:4]2[C:5]([N:24]([CH2:29][CH2:30][S:31]([CH3:33])=[O:32])[S:25]([CH3:28])(=[O:27])=[O:26])=[CH:6][C:7]3[O:11][C:10]([C:12]4[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=4)=[C:9]([C:19](=[N:21][OH:22])[NH2:20])[C:8]=3[CH:23]=2)[CH2:3][CH2:2]1.[CH:34](=O)[CH3:35].C([OH:39])C>O>[CH:1]1([C:4]2[C:5]([N:24]([CH2:29][CH2:30][S:31]([CH3:33])(=[O:39])=[O:32])[S:25]([CH3:28])(=[O:27])=[O:26])=[CH:6][C:7]3[O:11][C:10]([C:12]4[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=4)=[C:9]([C:19]4[NH:20][CH:34]([CH3:35])[O:22][N:21]=4)[C:8]=3[CH:23]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 177Acetaldehyde2×HCID 702EthanolHCID 131733687HCID 131733687, compound

Product 1

HCID 178432463HCID 178432463, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of Example 12C (sulfone/sulfoxide mixture, 0.105 g) in ethanol (2 mL) and water (2 mL) was treated with acetaldehyde (1.92 mL, 34 mmol), and the reaction mixture was stirred at room temperature for 3 days. Additional acetaldehyde (1 mL) was added and stirring was continued at room temperature for 3 more days. The reaction mixture was partitioned between ethyl acetate (50 mL) and water (50 mL). The organic layer was washed with water (3×25 mL), dried over anhydrous MgSO4, filtered, and concentrated in vacuo. Purification by silica gel flash chromatography eluting with a gradient of 1:10 ethyl acetate/hexane to 1:2 ethyl acetate/hexane, then 2:1 ethyl acetate/hexane containing 2% methanol, followed by 2% methanol/dichloromethane, afforded the title compound (0.0115 g). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.58 (dd, J=5.80, 2.90 Hz, 1H), 0.89 (dd, J=9.61, 4.27 Hz, 1H), 0.98-1.14 (m, 2H), 1.38 (t, J=5.42 Hz, 3H), 2.28-2.35 (m, 1H), 3.03 (s, 3H), 3.23 (s, 3H), 3.99-4.20 (m, 2H), 5.73-5.81 (m, 1H), 7.27-7.33 (m, 2H), 7.38-7.47 (m, 2H), 7.92 (s, 1H), 8.02 (dd, J=8.24, 5.49 Hz, 2H); MS (ESI+) m/z 536 (M+H)+; (ESI−) m/z 534 (M−H)−.

Workup

  1. stirringstirring
  2. customwas continued at room temperature for 3 more days
  3. customThe reaction mixture was partitioned between ethyl acetate (50 mL) and water (50 mL)
  4. washThe organic layer was washed with water (3×25 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by silica gel flash chromatography
  9. washeluting with a gradient of 1:10 ethyl acetate/hexane to 1:2 ethyl acetate/hexane

Sources & evidence

ORD record
ord-e6621290ca854a83971be7104b8edb40
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Reaction notes

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