Isobutyl mercaptan → 3-(N-t-butoxycarbonyl-N-methylamino)propyl isobutyl sulfide

HRID 847558Notes

Reaction equation

HRID 847558 reaction equation
[H-].[Na+].CS(O[CH2:8][CH2:9][CH2:10][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH3:12])(=O)=O.[CH3:20][CH:21]([CH3:24])[CH2:22][SH:23]>O1CCCC1>[CH2:22]([S:23][CH2:8][CH2:9][CH2:10][N:11]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH3:12])[CH:21]([CH3:24])[CH3:20]

Participants

5

Reactant 3

HCID 10558Isobutyl mercaptan2×HCID 24758Sodium hydride2×HCID 197540213-((Tert-butoxycarbonyl)(methyl)amino)propyl methanesulfonate

Product 1

HCID 197538633-(N-t-butoxycarbonyl-N-methylamino)propyl isobutyl sulfideYield 28.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of sodium hydride (336 mg: 60% dispersion in oil) in anhydrous tetrahydrofuran (12 ml) was added a solution of 3-(N-t-butoxycarbonyl-N-methylamino)propyl methanesulfonate (2.139 g) in tetrahydrofuran (10 ml) dropwise over 5 minutes. After being stirred for 30 minutes, the mixture was cooled to 0° C., and 2-methyl-1-propanethiol (758 mg) was added dropwise at 0°-5° C. The mixture was then allowed to warm to ambient temperature and stirred for 24 hours. Additional 168 mg of sodium hydride and 379 mg of 2-methyl-1-propanethiol was added above the same condition. After being stirred for another 16 hours, the solvent was evaporated and the resulting residue was dissolved in ethyl acetate (100 ml). The solution was washed with 0.5 N hydrochloric acid (100 ml), water (100 ml), aqueous sodium bicarbonate (100 ml), water (100ml), and brine (100 ml) successively, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel eluting with a mixture of n-hexane and ethyl acetate (6:4 V/V) to give 3-(N-t-butoxycarbonyl-N-methylamino)propyl isobutyl sulfide (595 mg) as an oil.

Workup

  1. temperatureto warm to ambient temperature
  2. stirringstirred for 24 hours
  3. stirringAfter being stirred for another 16 hours
  4. customthe solvent was evaporated
  5. dissolutionthe resulting residue was dissolved in ethyl acetate (100 ml)
  6. washThe solution was washed with 0.5 N hydrochloric acid (100 ml), water (100 ml), aqueous sodium bicarbonate (100 ml), water (100ml), and brine (100 ml) successively
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was chromatographed on silica gel eluting with a mixture of n-hexane and ethyl acetate (6:4 V/V)

Sources & evidence

ORD record
ord-8917365ae52546d380809da0dfd6d3c2
Source dataset
uspto-grants-1992_08
Patent number
US05142048

Reaction notes

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