Water → 3-methyl-4-[2-[N-(5-methyl-2-furylsulfonyl)amino]4,5-dimethylphenoxymethyl]benzoic acid methyl ester

HRID 2057102Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:22])[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[NH2:20])=[C:6]([CH3:21])[CH:5]=1.[CH3:23][C:24]1[O:28][C:27]([S:29](Cl)(=[O:31])=[O:30])=[CH:26][CH:25]=1.C(OCC)(=O)C.O>N1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:22])[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:29]([C:27]2[O:28][C:24]([CH3:23])=[CH:25][CH:26]=2)(=[O:31])=[O:30])=[C:6]([CH3:21])[CH:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 4-(2-amino-4,5-dimethylphenoxymethyl)-3-methylbenzoic acid methyl ester prepared in reference example 2 (632 mg) in pyridine (4 ml) was cooled to 0° C., then 5-methylfuran-2-sulfonyl chloride (490 mg) was added dropwise thereto. After the solution was stirred for 1 hour at room temperature, the reaction mixture was diluted by ethyl acetate, and poured into water. The organic layer was washed, dried, concentrated under reduced pressure. The residue was washed by mixed solvent of diisopropylether and hexane to give the title compound (875 mg) having the following physical data.

Workup

washThe organic layer was washed
customdried
concentrationconcentrated under reduced pressure
washThe residue was washed
additionby mixed solvent of diisopropylether and hexane

Sources & evidence

ORD record: ord-879de37b8929486ba4160a3674d4041c
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07335776B2

Reaction notes

Loading…