Ethanol → [4-(3,5-Di-tert-butyl-4-methoxy-phenylethynyl)-2-fluoro-phenyl]-acetic Acid

HRID 2299529Notes

Reaction equation

HRID 2299529 reaction equation
C[O:2][C:3](=[O:30])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:18]=[C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:16]([O:23][CH3:24])=[C:15]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:14]=2)=[CH:7][C:6]=1[F:29].[OH-].[Na+].C(O)C.O>C(#N)C>[C:19]([C:17]1[CH:18]=[C:13]([C:12]#[C:11][C:8]2[CH:9]=[CH:10][C:5]([CH2:4][C:3]([OH:30])=[O:2])=[C:6]([F:29])[CH:7]=2)[CH:14]=[C:15]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:16]=1[O:23][CH3:24])([CH3:20])([CH3:21])[CH3:22]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 695488624-(3,5-Di-tert-butyl-4-methoxy-phenylethynyl)-2-fluoro-phenyl-acetic acid methyl ester2×

Product 1

HCID 10111372[4-(3,5-Di-tert-butyl-4-methoxy-phenylethynyl)-2-fluoro-phenyl]-acetic Acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Following General Procedure I and using [4-(3,5-di-tert-butyl-4-methoxy-phenylethynyl)-2-fluoro-phenyl]-acetic acid methyl ester (Compound 144, 0.122 g, 0.29 mmol), 5M aqueous sodium hydroxide solution (1 mL) and ethanol (4 mL), followed preparative reverse phase HPLC using 10% water in acetonitrile as the mobile phase, the title compound was obtained as a white solid (0.077 g, 65%).

Sources & evidence

ORD record
ord-771dda63fde144b7b0732578f3bb8f3f
Source dataset
uspto-grants-2002_12
Patent number
US06495552B2

Reaction notes

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