Methyl p-toluenesulfonate → HCID 178482724, compound

HRID 230392Notes

Reaction equation

HRID 230392 reaction equation
[CH2:1]([NH:8][C@@H:9]([C:20]1[NH:21][CH:22]=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:24]=1)[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(C1C=CC(C)=CC=1)(O[CH3:35])(=O)=O.CC([O-])(C)C.[K+].C(=O)(O)[O-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH2:1]([N:8]([CH3:35])[C@@H:9]([C:20]1[NH:21][CH:22]=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:24]=1)[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6645Methyl p-toluenesulfonateHCID 516892Sodium BicarbonateHCID 23665647Potassium tert-butoxideHCID 178420366HCID 178420366, compound

Product 1

HCID 178482724HCID 178482724, compoundYield 4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
23 °C

Procedure

(1R)-N-benzyl-2-(1H-indol-3-yl)-1-(4-phenyl-1H-imidazol-2-yl)ethanamine (0.5 g; 0.00127 mol; prepared according to experimental conditions analogous to that of example 38 using the appropriate starting compounds and reaction products) was diluted in 25 ml tetrahydrofurane. Methyl tosylate (0.24 g; 0.00127 mol) was added to the preceding at about 23° C. and then potassium tert-butylate (0.15 g; 0.00127 mol) was added quite slowly. Agitation at about 23° C. was maintained for about two hours and then the mixture was heated to around 60° C. for about 8 hours. The solvent was evaporated and the residue obtained taken up in ethyl acetate and a 10% sodium bicarbonate solution. After phase separation, the organic phase was washed with water and dried over magnesium sulfate. The solvent was then evaporated. After purification over a silica column (eluent: ethyl acetate-heptane/7-3), a light beige solid was obtained in the form of a glue (yield of 4%). Free base. Melting point: 110-112° C. MH+=407.3.

Workup

  1. customprepared
  2. customcompounds and reaction products)
  3. temperaturethe mixture was heated to around 60° C. for about 8 hours
  4. customThe solvent was evaporated
  5. customthe residue obtained
  6. customAfter phase separation
  7. washthe organic phase was washed with water
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was then evaporated
  10. customAfter purification over a silica column (eluent: ethyl acetate-heptane/7-3)
  11. customa light beige solid was obtained in the form of a glue (yield of 4%)

Sources & evidence

ORD record
ord-e0c4ca7d10f74dc9835f7b92849cbf86
Source dataset
uspto-grants-2009_07
Patent number
US07566734B2

Reaction notes

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