Hydrochloric Acid → Methyl 3-[N-(p-chlorobenzyl)-5-hydroxyindol-2-yl]-2,2-dimethylpropanoate

HRID 1769343Notes

Reaction equation

HRID 1769343 reaction equation
[Cl:1][C:2]1[CH:31]=[CH:30][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](SC(C)(C)C)=[C:8]2[CH2:23][C:24]([CH3:29])([CH3:28])[C:25]([OH:27])=[O:26])=[CH:4][CH:3]=1.[CH2:32](S)C.[Al+3].[Cl-].[Cl-].[Cl-].Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([OH:16])=[CH:13][CH:14]=3)[CH:9]=[C:8]2[CH2:23][C:24]([CH3:29])([CH3:28])[C:25]([O:27][CH3:32])=[O:26])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 149805763-[N-(p-Chlorobenzyl)-3-(t-butylthio)-5-methoxyindol-2-yl]-2,2-dimethylpropanoic acid

Product 1

HCID 14980565Methyl 3-[N-(p-chlorobenzyl)-5-hydroxyindol-2-yl]-2,2-dimethylpropanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 1.0 g of 3-[N-(p-chlorobenzyl)-3-(t-butylthio)-5-methoxyindol-2-yl]-2,2-dimethylpropanoic acid (from Example 1 Step B) in 50 mL of CH2Cl2 was treated with 1.3 mL of ethanethiol and 3.47 g of AlCl3 at 0° C. under argon. After 40 min the mixture was poured onto 50 mL 1N HCl, extracted with 3×50 mL of CH2Cl2 washed with 2×50 mL of H2O, dried with MgSO4 and the solvent removed. The residue was dissolved in 10 mL ether and ethereal diazomethane added until all the acid was consumed. The excess solvent was removed and the residue chromatographed on silica gel to afford the title compound.

Workup

  1. extractionextracted with 3×50 mL of CH2Cl2
  2. washwashed with 2×50 mL of H2O
  3. dry with materialdried with MgSO4
  4. customthe solvent removed
  5. dissolutionThe residue was dissolved in 10 mL ether
  6. additionethereal diazomethane added until all the acid
  7. customwas consumed
  8. customThe excess solvent was removed
  9. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-a95f680ae3e341b291aeb87ba1d83ced
Source dataset
uspto-grants-1995_01
Patent number
US05380850

Reaction notes

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