Potassium Hydroxide → tert-Butyl [4-(4-sulfanylphenyl)butyl]carbamate

HRID 1175720Notes

Reaction equation

HRID 1175720 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]C(=O)N(C)C)=[CH:15][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+]>CO.O>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([SH:19])=[CH:17][CH:18]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 59750593N-tert-Butoxycarbonyl-4-[4-(dimethylcarbamoylthio)phenyl]butylamine

Product 1

HCID 59750597tert-Butyl [4-(4-sulfanylphenyl)butyl]carbamateYield 45.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

N-tert-Butoxycarbonyl-4-[4-(dimethylcarbamoylthio)phenyl]butylamine 37 (0.35 g, 1.02 mmol) was dissolved in MeOH (8 mL). KOH (0.19 g, 3.4 mmol) dissolved in water (2 ml) was added. The mixture was stirred under reflux for 6 h and cooled to room temperature. The solvent was removed under reduced pressure. The residue was dissolved in water and acidified with 5% aqueous HCl to pH ˜5. The solvent was removed again under reduced pressure and the residue was purified by flash chromatography over silica gel (hexane/ethyl acetate, 3:1, v/v) to give the desired thiophenol 38 (0.13 g, 45%) as a clear oil. 1H NMR (300 MHz, CDCl3) δ 1.43 (s, 9H), 1.49 (m, 2H) 1.59 (m, 2H), 2.57 (t, 2H), 3.12 (m, 2H), 3.38 (s, 1H), 4.47 (br s, 1H), 7.04 (d, 2H), 7.19 (d, 2H).

Workup

  1. additionwas added
  2. temperatureunder reflux for 6 h
  3. customThe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in water
  5. customThe solvent was removed again under reduced pressure
  6. customthe residue was purified by flash chromatography over silica gel (hexane/ethyl acetate, 3:1

Sources & evidence

ORD record
ord-1ca5451582f542f088ff5187a01aeda9
Source dataset
uspto-grants-2010_11
Patent number
US07842697B2

Reaction notes

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