HCID 11100666, compound → HCID 11782744, compound
Reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:23])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)=[CH:6][C:5]=1[O:24][CH3:25].[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[OH:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:23])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:20])[F:21])[CH:14]=2)=[CH:6][C:5]=1[O:24][CH3:25]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
2-Methoxy-4-[2-(3-trifluoromethylphenyl)acetylamino]benzoic acid methyl ester (2.0 g, 5.4 mmol) was dissolved in dry DCM (100 mL) under nitrogen and cooled to −20° C. Diisobutylaluminum hydride (1.2 M in toluene, 18.9 mmol, 16 mL) was dropwise added over 40min. The reaction mixture was heated to 20° C. and stirred at this temperature for 2 hr. After dilution with DCM (100 mL) the reaction mixture was quenched by dropwise addition of water (10 mL) at 20-25° C. The mixture was filtered after 16 hr and the organic phase was dried (magnesium sulphate), filtered and concentrated in vacuo to give crude N-(4-hydroxymethyl-3-methoxyphenyl)-2-(3-trifluoromethylphenyl)acetamide that was purified by column chromatography on silica (30 g) using heptane and ethyl acetate (3:2) as eluent.
Workup
- temperatureThe reaction mixture was heated to 20° C.
- customAfter dilution with DCM (100 mL) the reaction mixture was quenched by dropwise addition of water (10 mL) at 20-25° C
- filtrationThe mixture was filtered after 16 hr
- dry with materialthe organic phase was dried (magnesium sulphate)
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-a165a58970e34611af599d9079ad02f0
- Source dataset
- uspto-grants-2003_09
- Patent number
- US06613942B1
Reaction notes
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