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

HRID 841478Notes

Reaction equation

HRID 841478 reaction equation
[CH2:1]([CH2:8][NH:9][C:10]1([C:13]2[CH:18]=[CH:17][C:16]([C:19]#[C:20][C:21]3[CH:31]=[CH:30][C:24]([C:25]([O:27]CC)=[O:26])=[CH:23][CH:22]=3)=[CH:15][CH:14]=2)[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C.O1CCCC1>[CH2:1]([CH2:8][NH:9][C:10]1([C:13]2[CH:18]=[CH:17][C:16]([C:19]#[C:20][C:21]3[CH:31]=[CH:30][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=3)=[CH:15][CH:14]=2)[CH2:11][CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69548908HCID 69548908, compound2×

Product 1

HCID 225690014-[4-(1-Benzylmethylamino-cyclopropyl)-phenylethynyl]-benzoic acidYield 75%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Using General Procedure I; a solution of ethyl 4-{4-[1-(benzylmethylamino)-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-c372199c38df4207aea156f6abe42559
Source dataset
uspto-grants-2002_04
Patent number
US06369225B1

Reaction notes

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