Sodium Hydroxide → 4-[4-(1-Benzylmethylamino-cyclopropyl)-phenylethynyl]-benzoic acid

HRID 1935932Notes

Reaction equation

HRID 1935932 reaction equation
C([N:8]([CH3:31])[C:9]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]#[C:19][C:20]3[CH:30]=[CH:29][C:23]([C:24]([O:26]CC)=[O:25])=[CH:22][CH:21]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10]1)C1C=CC=CC=1.[OH-].[Na+]>C(O)C.O1CCCC1>[CH2:9]([CH2:31][NH:8][C:9]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]#[C:19][C:20]3[CH:21]=[CH:22][C:23]([C:24]([OH:26])=[O:25])=[CH:29][CH:30]=3)=[CH:16][CH:17]=2)[CH2:11][CH2:10]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22568953HCID 22568953, compound2×

Product 1

HCID 225690014-[4-(1-Benzylmethylamino-cyclopropyl)-phenylethynyl]-benzoic acidYield 147.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Using General Procedure I; a solution of ethyl 4-{4-[1-(benzyl-methylamino)-cyclopropyl]-phenylethynyl}-benzoate (Compound 115, 65.0 mg, 0.16 mmol) in ethanol (3 mL) and tetrahydrofuran (3 mL) was treated with NaOH (80.0 mg, 2.0 mmols, 2.0 mL of a 1N aqueous solution) and stirred overnight at room temperature. Work-up afforded 45.0 mg (75%) of the title compound as a solid.

Sources & evidence

ORD record
ord-6414c8c5f2024aef9b0ba65c845ad9f9
Source dataset
uspto-grants-2002_05
Patent number
US06387892B1

Reaction notes

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