Sodium Hydroxide → HCID 86689980, compound

HRID 1754048Notes

Reaction equation

HRID 1754048 reaction equation
C([O:4][CH:5]([CH2:19][CH2:20][S:21]([CH3:23])=[O:22])[C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:7])(=O)C.[OH-].[Na+]>CO.ClCCl>[CH2:9]([NH:8][C:6](=[O:7])[CH:5]([OH:4])[CH2:19][CH2:20][S:21]([CH3:23])=[O:22])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86689979HCID 86689979, compound

Product 1

HCID 86689980HCID 86689980, compoundYield 70.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(decylamino)-4-(methylsulfinyl)-1-oxobutan-2-yl acetate (22.4 g, 63.4 mmol) in methanol (300 mL) was added 2.5 N NaOH (39 mL, 97.5 mmol) and the resulting solution was stirred at room temperature for 5 hrs. The reaction was quenched with concentrated HCl (12.5 mL) and then evaporated to a small volume. The resulting mixture was treated with EtOAc (200 mL) and then washed with 1N HCl (150 mL), saturated sodium bicarbonate (50 mL), dried over magnesium sulfate, filtered and evaporated to give a solid. The solid was dissolved in dichloromethane and purified by silica gel chromatography with 0-10% methanol/dichloromethane. The desired fractions were collected and evaporated to give a white solid (13.6 g, 70%). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.85 (t, J=6.83 Hz, 3 H) 1.15-1.32 (m, 14 H) 1.32-1.46 (m, 2 H) 1.75-1.87 (m, 1 H) 1.94-2.06 (m, 1 H) 2.51 (d, J=1.27 Hz, 3 H) 2.58-2.88 (m, 2 H) 3.00-3.12 (m, 2 H) 3.89-4.02 (m, 1 H) 5.69 (d, J=5.40 Hz, 1 H) 7.76 (t, J=5.56 Hz, 1 H). m/z 306 (MH+).

Workup

  1. customThe reaction was quenched with concentrated HCl (12.5 mL)
  2. customevaporated to a small volume
  3. additionThe resulting mixture was treated with EtOAc (200 mL)
  4. washwashed with 1N HCl (150 mL), saturated sodium bicarbonate (50 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto give a solid
  9. custompurified by silica gel chromatography with 0-10% methanol/dichloromethane
  10. customThe desired fractions were collected
  11. customevaporated

Sources & evidence

ORD record
ord-46d89498815f461d8ed6eedf27df196e
Source dataset
uspto-grants-2015_10
Patent number
US09169203B2

Reaction notes

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