Ethanol → HCID 70158340, compound

HRID 2299514Notes

Reaction equation

HRID 2299514 reaction equation
[CH:1]1([N:4]([CH2:7][C:8]2[CH:13]=[CH:12][C:11](C#CC3C=CC(C(OCC)=O)=CC=3)=[CH:10][C:9]=2[CH:27]([CH3:29])[CH3:28])[CH2:5][CH3:6])[CH2:3][CH2:2]1.[OH-:30].[Na+].[CH2:32]([OH:34])[CH3:33]>O1CCCC1>[CH:1]1([N:4]([CH2:7][C:8]2[C:9]([CH:27]([CH3:29])[CH3:28])=[CH:10][CH:11]=[CH:12][C:13]=2[C:28]#[C:27][C:9]2[CH:10]=[CH:11][C:33]([C:32]([OH:30])=[O:34])=[CH:7][CH:8]=2)[CH2:5][CH3:6])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 22568791Ethyl 4-{4-[(cyclopropyl-ethyl-amino)-methyl]-3-isopropyl-phenylethynyl}-benzoate2×

Product 1

HCID 70158340HCID 70158340, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using General Procedure I; a solution of ethyl 4-{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-d685e1b424fa4a06b087292aa8988a51
Source dataset
uspto-grants-2002_12
Patent number
US06495552B2

Reaction notes

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