Tetrahydrofuran → HCID 86757949, compound

HRID 841508Notes

Reaction equation

HRID 841508 reaction equation
C1([CH2:4][CH2:5][NH:6][CH2:7][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][C:9]=2[CH:27]([CH3:29])[CH3:28])CC1.[OH-].[Na+].O1[CH2:36][CH2:35][CH2:34]C1>C(O)C>[CH:34]1([N:6]([CH2:7][C:8]2[C:9](=[C:27]([CH3:29])[CH3:28])[CH2:10][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:12][CH:13]=2)[CH2:5][CH3:4])[CH2:35][CH2:36]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 69548849HCID 69548849, compound2×

Product 1

HCID 86757949HCID 86757949, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Using General Procedure I; a solution of ethyl 4-{4-[(cyclopropylethyl-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-60cd9ce785394446b4cb4613c520d2c5
Source dataset
uspto-grants-2002_04
Patent number
US06369225B1

Reaction notes

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