Hydrochloric Acid → 3-(1H-indazol-5-yl)-2-methyl-3-phenylpropanoic acid

HRID 563425Notes

Reaction equation

HRID 563425 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]([CH3:16])[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:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:11]([CH3:16])[C:12]([OH:14])=[O:13])=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59252770methyl 3-(1H-indazol-5-yl)-2-methyl-3-phenylpropanoate

Product 1

HCID 670058283-(1H-indazol-5-yl)-2-methyl-3-phenylpropanoic acidYield 82%

Reagents, catalysts & solvents 1

HCID 86640187NaOH MeOH DMSOSolvent

Procedure

Each diastereomer of methyl 3-(1H-indazol-5-yl)-2-methyl-3-phenylpropanoate 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 27 mg (82% yield, 2 steps) and 35 mg of the diastereomers of acid 3-(1H-indazol-5-yl)-2-methyl-3-phenylpropanoic acid. MS found: (M+H)+=281.

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-b0705ba7c89043378196144ab2a9bd9b
Source dataset
uspto-grants-2011_11
Patent number
US08067447B2

Reaction notes

Loading…