Methyl p-toluenesulfonate → HCID 178482724, compound

HRID 2065977Notes

Reaction equation

HRID 2065977 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 under experimental conditions similar to that of Example 38 and using suitable starting reagents and reaction products) is diluted in 25 ml of tetrahydrofuran. Methyl tosylate (0.24 g; 0.00127 mol) is added to the previous solution at 23° C. then potassium tert-butylate (0.15 g; 0.00127 mol) is added fairly slowly. Stirring is maintained for two hours at 23° C. then the mixture is heated to about 60° C. for eight hours. The solvent is evaporated off and the residue obtained taken up in ethyl acetate and a 10% solution of sodium bicarbonate. After decantation, the organic phase is washed with water and dried over magnesium sulphate. The solvent is then evaporated off. After purification on a silica column (eluent: ethyl acetate-heptane/7-3), a light beige-coloured solid is obtained in the form of a paste (yield of 4%). Free base. Melting point: 110-112° C.

Workup

  1. customprepared under experimental conditions similar to that of Example 38
  2. customreagents and reaction products)
  3. temperaturethe mixture is heated to about 60° C. for eight hours
  4. customThe solvent is evaporated off
  5. customthe residue obtained
  6. washAfter decantation, the organic phase is washed with water
  7. dry with materialdried over magnesium sulphate
  8. customThe solvent is then evaporated off
  9. customAfter purification on a silica column (eluent: ethyl acetate-heptane/7-3)
  10. customa light beige-coloured solid is obtained in the form of a paste (yield of 4%)

Sources & evidence

ORD record
ord-fbefd4b63a164143a43b5fa61af8831e
Source dataset
uspto-grants-2012_10
Patent number
US08288560B2

Reaction notes

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