Sodium Hydroxide → HCID 9925134, compound

HRID 1936129Notes

Reaction equation

HRID 1936129 reaction equation
[CH2:1]([N:4]([CH2:27][CH2:28][CH3:29])[C:5]1([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]3[CH:26]=[CH:25][C:19]([C:20]([O:22]CC)=[O:21])=[CH:18][CH:17]=3)=[CH:10][CH:9]=2)[CH2:7][CH2:6]1)[CH2:2][CH3:3].[OH-].[Na+]>C(O)C.O1CCCC1>[CH2:27]([N:4]([CH2:1][CH2:2][CH3:3])[C:5]1([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]3[CH:17]=[CH:18][C:19]([C:20]([OH:22])=[O:21])=[CH:25][CH:26]=3)=[CH:10][CH:9]=2)[CH2:6][CH2:7]1)[CH2:28][CH3:29]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22568957HCID 22568957, compound2×

Product 1

HCID 9925134HCID 9925134, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Using General Procedure I; a solution of ethyl 4-[4-(1-dipropylamino-cyclopropyl)-phenylethynyl]-benzoate (Compound 109, 51.0 mg, 0.13 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 32.0 mg (70%) of the title compound as a colorless solid.

Sources & evidence

ORD record
ord-3ecd24e8a2504a49b6f619fc9c86c5db
Source dataset
uspto-grants-2002_05
Patent number
US06387951B1

Reaction notes

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