Isobutyl iodide → 3-methyl-4-[2-[N-isobutyl-N-(5-methyl-2-furylsulfonyl)amino]-4,5-dimethylphenoxymethyl]benzoic Acid Methyl Ester

HRID 1866203Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]2[CH:17]=[C:16]([CH3:18])[C:15]([CH3:19])=[CH:14][C:13]=2[NH:20][S:21]([C:24]2[O:25][C:26]([CH3:29])=[CH:27][CH:28]=2)(=[O:23])=[O:22])=[C:6]([CH3:30])[CH:5]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:38](I)[CH:39]([CH3:41])[CH3:40].C(OCC)(=O)C.O>CN(C)C(=O)C>[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]2[CH:17]=[C:16]([CH3:18])[C:15]([CH3:19])=[CH:14][C:13]=2[N:20]([CH2:38][CH:39]([CH3:41])[CH3:40])[S:21]([C:24]2[O:25][C:26]([CH3:29])=[CH:27][CH:28]=2)(=[O:23])=[O:22])=[C:6]([CH3:30])[CH:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 3-methyl-4-[2-[N-(5-methyl-2-furylsulfonyl)amino]4,5-dimethylphenoxymethyl]benzoic acid methyl ester prepared in Reference Example 3 (870 mg) in N,N-dimethylacetamide (2 ml), cesium carbonate (1.37 g) and isobutyl iodide (0.36 ml) were added and the mixture was stirred for 1 hour at 100° C. The reaction mixture was allowed to cool and poured into ethyl acetate-water (40 ml-40 ml). The organic layer was washed, dried and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (toluene-ethyl acetate) to give the title compound (855 mg) having the following physical data.

Workup

additionwere added
temperatureto cool
washThe organic layer was washed
customdried
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography on silica gel (toluene-ethyl acetate)

Sources & evidence

ORD record: ord-cb26ba6a38da4379a976e1ea6f8e80e3
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07629369B2

Reaction notes

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