p-Toluenesulfonic acid monohydrate → HCID 86622848, compound

HRID 1094127Notes

Reaction equation

HRID 1094127 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-8fa4f314ffd843d88dd11bca51bec1ff
Source dataset
uspto-grants-2012_03
Patent number
US08133891B2

Reaction notes

Loading…