Dichloromethane → 2-(4-tert-Butylphenoxy)-N-{3-hydroxy-4-[(methylsulfonyl)amino]benzyl}acetamide

HRID 1350836Notes

Reaction equation

[C:1]([C:5]1[CH:29]=[CH:28][C:8]([O:9][CH2:10][C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[C:17]([O:26]C)[CH:16]=2)=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl.B(Br)(Br)Br>C(OCC)(=O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH2:10][C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][S:22]([CH3:25])(=[O:23])=[O:24])=[C:17]([OH:26])[CH:16]=2)=[O:12])=[CH:28][CH:29]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-(4-tert-butylphenoxy)-N-{3-methoxy-4-[(methylsulfonyl)amino]benzyl}acetamide (Example 11) (446 mg, 1.06 mmol) in methylene dichrolide (20 ml) was added 1.0 M methylene dichloride solution of boron(III)bromide (5.3 ml, 5.3 mmol) at 0° C. After being stirred for 1.5 hours at 0° C., the mixture was quenched with water and crude residue was extracted with methylene dichloride. The organic layer was separated, then washed with brine, dried over magnesium sulfate. Then, filtration to remove magnesium sulfate, evaporation under removed pressure gave the residue, which was applied to a silica gel chromatography column and eluted with a volume mixture of hexane : ethyl acetate (2/3) to furnish 293 mg (55% yield) of the title compound as a white solid.

Workup

customthe mixture was quenched with water and crude residue
extractionwas extracted with methylene dichloride
customThe organic layer was separated
washwashed with brine
dry with materialdried over magnesium sulfate
filtrationThen, filtration
customto remove
custommagnesium sulfate, evaporation
customunder removed pressure
customgave the residue, which
washeluted with a volume mixture of hexane

Sources & evidence

ORD record: ord-ead0fd19b6f749dba193f7ba7c691dc0
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07214824B2

Reaction notes

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