Sodium Hydroxide → HCID 86689977, compound

HRID 1754045Notes

Reaction equation

HRID 1754045 reaction equation
C([O:4][CH:5]([CH2:17][CH2:18][S:19]([CH3:21])=[O:20])[C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:7])(=O)C.[OH-].[Na+]>CO>[OH:4][CH:5]([CH2:17][CH2:18][S:19]([CH3:21])=[O:20])[C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86689976HCID 86689976, compound

Product 1

HCID 86689977HCID 86689977, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(methylsulfinyl)-1-(octylamino)-1-oxobutan-2-yl acetate (5.7 g, 17.87 mmol) in methanol (75 mL) was added 1M NaOH (26.8 mL, 26.8 mmol) and the resulting solution was stirred overnight. The reaction was evaporated to a small volume and treated with EtOAc (100 mL) and 1N HCl (100 mL). The layers were separated and the organic layer was dried over magnesium sulfate, filtered and evaporated. The crude material was purified by silica gel chromatography with 0-5% methanol/dichloromethane. The desired fractions were collected and evaporated to give a white solid (3.23 g, 65%). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.85 (t, J=6.83 Hz, 3 H) 1.24 (br. s., 10 H) 1.33-1.47 (m, 2 H) 1.73-1.89 (m, 1 H) 1.95-2.10 (m, 1 H) 2.51 (d, J=0.64 Hz, 3 H) 2.58-2.87 (m, 2 H) 2.99-3.14 (m, 2 H) 3.95 (dd, J=7.15, 4.29 Hz, 1 H) 5.69 (d, J=5.09 Hz, 1 H) 7.76 (t, J=5.40 Hz, 1 H). m/z 278 (MH+).

Workup

  1. customThe reaction was evaporated to a small volume
  2. additiontreated with EtOAc (100 mL) and 1N HCl (100 mL)
  3. customThe layers were separated
  4. dry with materialthe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude material was purified by silica gel chromatography with 0-5% methanol/dichloromethane
  8. customThe desired fractions were collected
  9. customevaporated

Sources & evidence

ORD record
ord-4a2487630cfb40a1ac695641acfcf959
Source dataset
uspto-grants-2015_10
Patent number
US09169203B2

Reaction notes

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