Diethyl Oxalate → N-{4-[3-(4-fluorobenzenesulfonyl)-4-hydroxyphenoxy]-3,5-dimethylphenyl}oxamic acid ethyl ester

HRID 2120307Notes

Reaction equation

[NH2:1][C:2]1[CH:25]=[C:24]([CH3:26])[C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([S:14]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH:8]=2)=[C:4]([CH3:27])[CH:3]=1.[C:28](OCC)(=[O:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30]>>[CH2:32]([O:31][C:29](=[O:30])[C:28]([NH:1][C:2]1[CH:25]=[C:24]([CH3:26])[C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([S:14]([C:17]3[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)(=[O:16])=[O:15])[CH:8]=2)=[C:4]([CH3:27])[CH:3]=1)=[O:34])[CH3:33]

Participants

Reactant 2

HCID 7268Diethyl Oxalate

HCID 223448764-(4-Amino-2,6-dimethylphenoxy)-2-(4-fluorobenzenesulfonyl)phenol

Product 1

HCID 10163263N-{4-[3-(4-fluorobenzenesulfonyl)-4-hydroxyphenoxy]-3,5-dimethylphenyl}oxamic acid ethyl ester

Conditions

Temperature: 180 °C

Procedure

A mixture of the title D compound, 4-(4-amino-2,6-dimethylphenoxy)-2-(4-fluoro-benzenesulfonyl)phenol (0.64 g, 1.65 mmol) and 2 mL of diethyl oxalate is heated at 180° C. for 3 h. The reaction is cooled to RT and diethyl oxalate is removed under vacuum. Chromatography on silica (eluant; EtOAc/hexane—1/3?2/3) affords N-{4-[3-(4-fluoro-benzenesulfonyl)-4-hydroxyphenoxy]-3,5-dimethylphenyl}oxamic acid ethyl ester: NMR (CDCl3) 1.46 (t, 3H, J=7.5), 2.06 (s, 6H), 4.42 (q, 2H, J=7.5), 6.90-6.98 (m, 3H), 7.22 (app t, 2H, J=8.3), 7.40 (s,2H), 7.87-7.93 (m, 2H), 8.87 (br s, 1H); ESI-MS 486 [M−1]−.

Workup

temperatureThe reaction is cooled to RT
customdiethyl oxalate is removed under vacuum

Sources & evidence

ORD record: ord-320bf583ee33483281dd782af6c5a3e9
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06689896B2

Reaction notes

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