Sodium Hydroxide → 4-{4-[(Cyclopropyl-ethyl-amino)-methyl]-3-isopropyl-phenylethynyl}-benzoic acid

HRID 381160Notes

Reaction equation

HRID 381160 reaction equation
C([O:3][C:4](=[O:29])[C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][N:20]([CH:23]3[CH2:25][CH2:24]3)[CH2:21][CH3:22])=[C:15]([CH:26]([CH3:28])[CH3:27])[CH:14]=2)=[CH:7][CH:6]=1)C.[OH-].[Na+]>C(O)C.O1CCCC1>[CH:23]1([N:20]([CH2:19][C:16]2[CH:17]=[CH:18][C:13]([C:12]#[C:11][C:8]3[CH:9]=[CH:10][C:5]([C:4]([OH:29])=[O:3])=[CH:6][CH:7]=3)=[CH:14][C:15]=2[CH:26]([CH3:27])[CH3:28])[CH2:21][CH3:22])[CH2:24][CH2:25]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22568791Ethyl 4-{4-[(cyclopropyl-ethyl-amino)-methyl]-3-isopropyl-phenylethynyl}-benzoate2×

Product 1

HCID 102699774-{4-[(Cyclopropyl-ethyl-amino)-methyl]-3-isopropyl-phenylethynyl}-benzoic acidYield 73.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Using General Procedure I; a solution of ethyl4-{4-[(cyclopropyl-ethyl-amino)-methyl]-3-isopropyl-phenylethynyl}-benzoate (Compound 133, 68.0 mg, 0.17 mmol) in ethanol (3 mL) and tetrahydrofuran (3 mL) was treated with NaOH (600.0 mg,15.0 mmols, 3.0 mL of a 5N aqueous solution) and stirred overnight at room temperature and then at 55° C. for 9 hours. Work-up followed by crystallization of the solid residue from hot CH3CN afforded 45.0 mg (72%) of the title compound as a pale-yellow solid.

Workup

  1. waitat 55° C. for 9 hours
  2. customWork-up followed by crystallization of the solid residue from hot CH3CN

Sources & evidence

ORD record
ord-6961df1ecfeb4a5883e4eecaeb374eda
Source dataset
uspto-grants-2001_10
Patent number
US06303785B1

Reaction notes

Loading…