Hydrochloric Acid → HCID 15229448, compound

HRID 1032976Notes

Reaction equation

HRID 1032976 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16]C)=[CH:13][CH:14]=3)[C:9]([CH3:18])=[C:8]2[CH2:19][C:20]([CH3:25])([CH3:24])[C:21]([OH:23])=[O:22])=[CH:4][CH:3]=1.[CH2:28](S)C.[Al+3].[Cl-].[Cl-].[Cl-].Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([OH:16])=[CH:13][CH:14]=3)[C:9]([CH3:18])=[C:8]2[CH2:19][C:20]([CH3:25])([CH3:24])[C:21]([O:23][CH3:28])=[O:22])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 117408193-[1-(4-Chlorobenzyl)-3-methyl-5-methoxyindol-2-yl]-2,2-dimethylpropanoic acid

Product 1

HCID 15229448HCID 15229448, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.05 g (2.7 mmol) of 3-[1-(4-chlorobenzyl)-3-methyl-5-methoxyindol-2-yl]-2,2-dimethylpropanoic acid (EP 166,591, Example 22) and 800 μL of ethanethiol (10 mmol) in 20 mL of CH2Cl2 at -20° C. was added in portions 2.17 g (16 mmol) of AlCl3. The reaction turned light orange and was stirred at room temperature overnight. In the morning, the reaction was completed (tlc) and it was poured into a solution of 1N HCl and extracted 3x with CH2Cl2. The combined organic layers were washed with brine, dried (MgSO4), and filtered. The filtrate was evaporated and to the residual syrup (680 mg) was added 20 mL of Et2O followed by an ethereal solution of diazomethane. Evaporation of the solvent left the crude title compound which was used without further purification.

Workup

  1. extractionextracted 3x with CH2Cl2
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated and to the residual syrup (680 mg)
  6. additionwas added 20 mL of Et2O
  7. customEvaporation of the solvent
  8. waitleft the crude title compound which
  9. customwas used without further purification

Sources & evidence

ORD record
ord-dae2b51974254fb2bbd61b14b12a1aee
Source dataset
uspto-grants-1994_05
Patent number
US05308850

Reaction notes

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