Hydrochloric Acid → 3-[N-(p-Chlorobenzyl)-3-(t-butylthio)-5-methoxyindol-2-yl]-2,2-dimethylpropanoic acid

HRID 1590102Notes

Reaction equation

HRID 1590102 reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([S:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[C:8]2[CH2:23][C:24]([CH3:30])([CH3:29])[C:25]([O:27]C)=[O:26])=[CH:4][CH:3]=1.C1COCC1.[Li+].[OH-].Cl>CO>[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([S:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[C:8]2[CH2:23][C:24]([CH3:30])([CH3:29])[C:25]([OH:27])=[O:26])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 117625003-[1-(4-Chlorobenzyl)-3-(t-butylthio)-5-methoxyindol-2-yl]-2,2-dimethylpropanoic acid methyl ester

Product 1

HCID 149805763-[N-(p-Chlorobenzyl)-3-(t-butylthio)-5-methoxyindol-2-yl]-2,2-dimethylpropanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

The ester from Step 1 (51.3 g) was hydrolysed using 325 mL THF, 600 mL MeOH and 325 mL of 1N LiOH solution. The mixture was heated to 80° C. for 3 hours, then cooled, acidified with 1N HCl and extracted with 3×200 mL EtOAc. The organic phase was washed with H2O (2×150 mL) and dried (MgSO4). After removal of the solvent the title compound was obtained as a white solid, m.p. 190°-191° C.

Workup

  1. temperaturecooled
  2. extractionextracted with 3×200 mL EtOAc
  3. washThe organic phase was washed with H2O (2×150 mL)
  4. dry with materialdried (MgSO4)
  5. customAfter removal of the solvent the title compound
  6. customwas obtained as a white solid, m.p. 190°-191° C.

Sources & evidence

ORD record
ord-8592fba9e3d54c5fb7657ddaf1731e85
Source dataset
uspto-grants-1993_04
Patent number
US05202321

Reaction notes

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