Hydrochloric Acid → 3-(4-{6-[5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-1H-indol-2-yl}-3,5-dimethyl-phenyl)-2,2-dimethyl-propionic acid

HRID 1360806Notes

Reaction equation

HRID 1360806 reaction equation
C[O:2][C:3](=[O:37])[C:4]([CH3:36])([CH3:35])[CH2:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([C:13]2[NH:14][C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[C:17]([C:22]2[O:23][C:24]([C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=4)=[N:25][N:26]=2)[CH:16]=3)=[C:8]([CH3:34])[CH:7]=1.[OH-].[Na+].C1COCC1.Cl>CO.O>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]([C:24]2[O:23][C:22]([C:17]3[CH:16]=[C:15]4[C:20]([CH:21]=[C:13]([C:9]5[C:8]([CH3:34])=[CH:7][C:6]([CH2:5][C:4]([CH3:35])([CH3:36])[C:3]([OH:37])=[O:2])=[CH:11][C:10]=5[CH3:12])[NH:14]4)=[CH:19][CH:18]=3)=[N:26][N:25]=2)=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 14798Sodium Hydroxide3×HCID 669667913-(4-{6-[5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-1H-indol-2-yl}-3,5-dimethyl-phenyl)-2,2-dimethyl-propionic acid methyl ester

Product 1

HCID 252355043-(4-{6-[5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-1H-indol-2-yl}-3,5-dimethyl-phenyl)-2,2-dimethyl-propionic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Suspend 3-(4-{6-[5-(4-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-1H-indol-2-yl}-3,5-dimethyl-phenyl)-2,2-dimethyl-propionic acid methyl ester (262 mg, 0.510 mmol) in MeOH (2.6 mL)/1 N NaOH (2.6 mL) and heat to 50° C. for 3 h. Add THF (2.6 mL) and heat to 50° C. for 15 h. Add 1 N NaOH (2.6 mL), THF (2.6 mL), and NaOH (225 mg, 5.63 mmol) in water (1 mL). Heat the reaction at 50° C. until the ester is not observed by LC/MS. Concentrate the reaction under reduced pressure. Adjust the pH to 2 with 1 N HCl. Collect the resulting precipitate by filtration and rinse the solid with Et2O to afford a light yellow solid: (M+H)+ 500.2.

Workup

  1. temperatureHeat
  2. concentrationConcentrate
  3. customthe reaction under reduced pressure
  4. customCollect the resulting precipitate
  5. filtrationby filtration
  6. washrinse the solid with Et2O
  7. customto afford a light yellow solid

Sources & evidence

ORD record
ord-7f2b80454f5e41fba0136446202f7dfe
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

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