Sodium Hydroxide → HCID 86689982, compound

HRID 1754050Notes

Reaction equation

HRID 1754050 reaction equation
C([O:4][CH:5]([CH2:21][CH2:22][S:23]([CH3:25])=[O:24])[C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:7])(=O)C.[OH-].[Na+]>CO.ClCCl>[CH2:9]([NH:8][C:6](=[O:7])[CH:5]([OH:4])[CH2:21][CH2:22][S:23]([CH3:25])=[O:24])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86689983HCID 86689983, compound

Product 1

HCID 86689982HCID 86689982, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(dodecylamino)-4-(methylsulfinyl)-1-oxobutan-2-yl acetate (25 g, 62.6 mmol) in methanol (350 mL) was added 2.5 N NaOH (40 mL, 100 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 (16.7 g, 80%). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.85 (t, J=6.83 Hz, 3 H) 1.15-1.33 (m, 18 H) 1.33-1.46 (m, 2 H) 1.72-1.87 (m, 1 H) 1.92-2.09 (m, 1 H) 2.51 (d, J=1.27 Hz, 3 H) 2.56-2.87 (m, 2 H) 3.00-3.12 (m, 2 H) 3.90-4.00 (m, 1 H) 5.69 (d, J=5.40 Hz, 1 H) 7.71-7.82 (m, 1 H). m/z 334 (MH+).

Workup

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

Sources & evidence

ORD record
ord-47078a6cfdd94877b085ef5377827229
Source dataset
uspto-grants-2015_10
Patent number
US09169203B2

Reaction notes

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