Hydrochloric Acid → 3-(3-(tert-butylthio)-1-(4-chlorobenzyl)-5-(pyridin-2-ylmethoxy)-1H-indol-2-yl)-2,2-dimethylpropanoic acid

HRID 274417Notes

Reaction equation

HRID 274417 reaction equation
C([O:4][C:5](=[O:40])[C:6]([CH3:39])([CH3:38])[CH2:7][C:8]1[N:9]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=2)[C:10]2[C:15]([C:16]=1[S:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][C:13]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1)=[CH:12][CH:11]=2)C=C.CO.[Li+].[OH-].Cl>C1COCC1>[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([CH2:30][N:9]2[C:10]3[C:15](=[CH:14][C:13]([O:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)=[CH:12][CH:11]=3)[C:16]([S:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[C:8]2[CH2:7][C:6]([CH3:39])([CH3:38])[C:5]([OH:40])=[O:4])=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 152294413-[1-(4-Chlorobenzyl)-3-(t-butylthio)-5-(pyridin-2-ylmethyoxy)indol-2-yl]-2,2-dimethylpropanoic acid allyl ester

Product 1

HCID 98286303-(3-(tert-butylthio)-1-(4-chlorobenzyl)-5-(pyridin-2-ylmethoxy)-1H-indol-2-yl)-2,2-dimethylpropanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound from Step 1 (133 mg) was dissolved in THF (5 mL), MeOH (3 mL), and 1N LiOH (1.2 mL) and heated at 55° C. for 1 hour. After cooling to room temperature, the mixture was acidified with 1N HCl and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered, and evaporated to dryness. The residue was swished in ether/hexane, affording the title compound as a white solid, m.p. 186.2°-187.7° C.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-3b3f223e6a3d453a8769b4920cc904fe
Source dataset
uspto-grants-1995_02
Patent number
US05389650

Reaction notes

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