Tetrahydrofuran → HCID 117840102, compound

HRID 1520302Notes

Reaction equation

HRID 1520302 reaction equation
[CH3:1][CH:2]([CH3:40])[CH:3]([NH:20][C:21]1[CH:39]=[CH:38][C:24]([C:25]([N:27]2[CH2:32][CH2:31][CH2:30][C@@H:29]([C:33]([O:35]CC)=[O:34])[CH2:28]2)=[O:26])=[CH:23][CH:22]=1)[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:18]=[C:17]3[C:12]([CH2:13][CH2:14][CH2:15][CH2:16]3)=[N:11]2)=[CH:6][C:5]=1[CH3:19].C1COCC1.[OH-].[Na+]>C(O)C>[CH3:1][CH:2]([CH3:40])[CH:3]([NH:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]([N:27]2[CH2:32][CH2:31][CH2:30][C@@H:29]([C:33]([OH:35])=[O:34])[CH2:28]2)=[O:26])=[CH:38][CH:39]=1)[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:18]=[C:17]3[C:12]([CH2:13][CH2:14][CH2:15][CH2:16]3)=[N:11]2)=[CH:6][C:5]=1[CH3:19]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 131733106HCID 131733106, compound

Product 1

HCID 117840102HCID 117840102, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of ethyl (3R)-1-(4-((2-methyl-1-(2-methyl-4-(4,5,6,7-tetrahydro-2H-indazol-2-yl)phenyl)propyl)amino)benzoyl)piperidine-3-carboxylate (152.3 mg), THF (0.56 mL) and ethanol (0.56 mL) was added 1M aqueous sodium hydroxide solution (0.561 mL), and the mixture was stirred at room temperature for 1 hr. The solvent was evaporated under reduced pressure, the reaction mixture was neutralized with 1M hydrochloric acid (0.561 mL), and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (140.4 mg).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-86c8bccd06bb4afba23ad17edcf7d682
Source dataset
uspto-grants-2015_07
Patent number
US09073864B2

Reaction notes

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