Hydrochloric Acid → 3-[1-(4-Chlorobenzyl)-3-(t-butylthio)-5-(2-methylthiazol-4-ylmethoxy)indol-2-yl]-2,2-dimethylpropanoic acid

HRID 486094Notes

Reaction equation

HRID 486094 reaction equation
[Cl:1][C:2]1[CH:38]=[CH:37][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:17][C:18]4[N:19]=[C:20]([CH3:23])[S:21][CH:22]=4)=[CH:13][CH:14]=3)[C:9]([S:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[C:8]2[CH2:29][C:30]([CH3:36])([CH3:35])[C:31]([O:33]C)=[O:32])=[CH:4][CH:3]=1.CO.Cl>[Li+].[OH-].C1COCC1>[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[N:19]=[C:20]([CH3:23])[S:21][CH:22]=4)=[CH:13][CH:14]=3)[C:9]([S:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[C:8]2[CH2:29][C:30]([CH3:36])([CH3:35])[C:31]([OH:33])=[O:32])=[CH:37][CH:38]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 19097505Methyl 3-[1-(4-chlorobenzyl)-3-(t-butylthio)-5-(2-methylthiazol-4-ylmethoxy)indol-2-yl]-2,2-dimethylpropanoate

Product 1

HCID 190975043-[1-(4-Chlorobenzyl)-3-(t-butylthio)-5-(2-methylthiazol-4-ylmethoxy)indol-2-yl]-2,2-dimethylpropanoic acid

Reagents, catalysts & solvents 2

HCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the ester from Step 1 (22.5 g) in 118 mL 1N LiOH, 120 mL THF, and 65 mL MeOH was heated at 60° C. for 2 hours. The mixture was cooled, poured onto 1N HCl, and extracted with EtOAc (3×). After washing the organic phase twice with brine, the solution was dried (MgSo4) and evaporated. The residue was swished with ether/hexane 1:2 to give the title compound as a solid; m.p. 196.5°-198° C.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with EtOAc (3×)
  3. washAfter washing the organic phase twice with brine
  4. customthe solution was dried (MgSo4)
  5. customevaporated

Sources & evidence

ORD record
ord-9c6cf8e6006f4b808bb9d24f0059472c
Source dataset
uspto-grants-1994_03
Patent number
US05290798

Reaction notes

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