Hydrochloric Acid → 3-[1-(4-Chlorobenzyl)-3-methyl-5-(4-prop-2-ylthiazol-2-ylmethoxy)indol-2-yl]-2,2dimethylpropanoic acid

HRID 486092Notes

Reaction equation

HRID 486092 reaction equation
[Cl:1][C:2]1[CH:36]=[CH:35][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:17][C:18]4[S:19][CH:20]=[C:21]([CH:23]([CH3:25])[CH3:24])[N:22]=4)=[CH:13][CH:14]=3)[C:9]([CH3:26])=[C:8]2[CH2:27][C:28]([CH3:34])([CH3:33])[C:29]([O:31]C)=[O:30])=[CH:4][CH:3]=1.C1COCC1.[Li+].[OH-].Cl>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:17][C:18]4[S:19][CH:20]=[C:21]([CH:23]([CH3:24])[CH3:25])[N:22]=4)=[CH:13][CH:14]=3)[C:9]([CH3:26])=[C:8]2[CH2:27][C:28]([CH3:34])([CH3:33])[C:29]([OH:31])=[O:30])=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 19097506HCID 19097506, compound

Product 1

HCID 98492443-[1-(4-Chlorobenzyl)-3-methyl-5-(4-prop-2-ylthiazol-2-ylmethoxy)indol-2-yl]-2,2dimethylpropanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the ester (70 mg) from Step 1, 2 mL THF, 1 mL MeOH, and 1 mL 2N LiOH was stirred for 24 hours at room temperature. The mixture was poured onto 1N HCl, extracted 2× EtOAc, washed 2× brine, dried (MgSO4), and evaporated. The product was recrystallized from Et2O/hexane to give the title compound as a solid.

Workup

  1. extractionextracted 2× EtOAc
  2. washwashed 2× brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe product was recrystallized from Et2O/hexane

Sources & evidence

ORD record
ord-24f2b3d9dd94459ea9576b03988c495b
Source dataset
uspto-grants-1994_03
Patent number
US05290798

Reaction notes

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