p-Toluenesulfonic acid monohydrate → HCID 86622848, compound

HRID 551054Notes

Reaction equation

HRID 551054 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH2:19][CH2:20][C:21]([O:23]CC)=O)=[CH:5][N:6]2[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[O:23]=[C:21]1[NH:1][C:2]2[C:3]3[C:4](=[CH:5][N:6]([CH2:11][C:12]([O:14][C:15]([CH3:17])([CH3:18])[CH3:16])=[O:13])[C:7]=3[CH:8]=[CH:9][CH:10]=2)[CH2:19][CH2:20]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 57426210HCID 57426210, compound

Product 1

HCID 86622848HCID 86622848, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of ethyl 3-[4-amino-1-(2-tert-butoxy-2-oxoethyl)-1H-indol-3-yl]propanoate from Step C (1.00 g, 2.89 mmol) in toluene (50 mL) was added p-toluenesulfonic acid monohydrate (5 mg, 0.026 mmol) and the mixture was heated at reflux. After 2 h, the reaction was allowed to cool to ambient temperature and the mixture was washed with saturated aqueous NaHCO3 (10 mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH—100:0 to 92:8, to give the title compound. MS: m/z=301 (M+1).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux
  3. washthe mixture was washed with saturated aqueous NaHCO3 (10 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by silica gel chromatography
  8. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-7d4a4c8dca184764b18055abba01ebae
Source dataset
uspto-grants-2011_05
Patent number
US07947677B2

Reaction notes

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