Hydrochloric Acid → 3-(1H-indazol-5-yl)-2,3-diphenylpropanoic acid

HRID 563429Notes

Reaction equation

HRID 563429 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:12]([O:14]C)=[O:13])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.Cl>[OH-].[Na+].CO.CS(C)=O>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:12]([OH:14])=[O:13])=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59252820methyl 3-(1H-indazol-5-yl)-2,3-diphenylpropanoate

Product 1

HCID 866403063-(1H-indazol-5-yl)-2,3-diphenylpropanoic acidYield 82%

Reagents, catalysts & solvents 1

HCID 86640187NaOH MeOH DMSOSolvent

Procedure

Methyl 3-(1H-indazol-5-yl)-2,3-diphenylpropanoate was heated to 100° C. overnight in a mixture of 2 M NaOH/MeOH/DMSO (1:1:1). The next day, the reaction was cooled, acidified to pH 5 with HCl and extracted 2×EtOAc. The organic layers were washed with water×2, dried over MgSO4, filtered, concentrated in vacuo, and purified by HPLC to give 10 mg (82% yield) and 30 mg of the diastereomers of acid 3-(1H-indazol-5-yl)-2,3-diphenylpropanoic acid. MS found: (M+H)+=343.

Workup

  1. temperatureThe next day, the reaction was cooled
  2. extractionextracted 2×EtOAc
  3. washThe organic layers were washed with water×2
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by HPLC

Sources & evidence

ORD record
ord-fc3f71ad02e34ba590434d9217042dc2
Source dataset
uspto-grants-2011_11
Patent number
US08067447B2

Reaction notes

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