Ethanol → HCID 10269185, compound

HRID 841507Notes

Reaction equation

HRID 841507 reaction equation
C[O:2][C:3](=[O:27])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][NH:20][CH2:21][CH2:22]C3CC3)=[C:15]([CH3:26])[CH:14]=2)=[CH:7][CH:6]=1.[OH-].[Na+].O.[CH3:31][C:32]#N.[CH2:34](O)C>O1CCCC1>[CH:32]1([N:20]([CH2:19][C:16]2[CH:17]=[CH:18][C:13]([C:12]#[C:11][C:8]3[CH:9]=[CH:10][C:5]([CH2:4][C:3]([OH:2])=[O:27])=[CH:6][CH:7]=3)=[CH:14][C:15]=2[CH3:26])[CH2:21][CH3:22])[CH2:31][CH2:34]1

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 18373917Acetonitrile--water (1/1)HCID 131723181HCID 131723181, compound2×

Product 1

HCID 10269185HCID 10269185, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using General Procedure I; a solution of methyl(4-{4-[(cyclopropylethyl-amino)-methyl]-3-methyl-phenylethynyl}-phenyl)-acetate (Compound 129, 140.0 mg, 0.39 mmol) in ethanol (5 mL) and tetrahydrofuran (5 mL) was treated with NaOH (360.0 mg, 9.0 mmols, 3.0 mL of a 3N aqueous solution) and stirred overnight at room temperature. Work-up followed by HPLC (Partisil-10 pac 10% H2O—CH3CN) afforded the title compound.

Sources & evidence

ORD record
ord-de11c2bc7acd4165a25c29f8a7d8dd39
Source dataset
uspto-grants-2002_04
Patent number
US06369225B1

Reaction notes

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