Sodium Hydroxide → {4-[4-(2-Nitro-4-trifluoromethanesulfonyl-phenoxy)-benzenesulfonyl]-phenoxy}-acetic acid

HRID 1358764Notes

Reaction equation

C([O:3][C:4](=[O:39])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]3[CH:28]=[CH:27][C:26]([S:29]([C:32]([F:35])([F:34])[F:33])(=[O:31])=[O:30])=[CH:25][C:24]=3[N+:36]([O-:38])=[O:37])=[CH:18][CH:17]=2)(=[O:15])=[O:14])=[CH:9][CH:8]=1)C.[OH-].[Na+]>C(O)(C)C.O1CCCC1>[N+:36]([C:24]1[CH:25]=[C:26]([S:29]([C:32]([F:35])([F:34])[F:33])(=[O:30])=[O:31])[CH:27]=[CH:28][C:23]=1[O:22][C:19]1[CH:18]=[CH:17][C:16]([S:13]([C:10]2[CH:9]=[CH:8][C:7]([O:6][CH2:5][C:4]([OH:39])=[O:3])=[CH:12][CH:11]=2)(=[O:15])=[O:14])=[CH:21][CH:20]=1)([O-:38])=[O:37]

Participants

Conditions

Temperature: 35 °C

Procedure

A mixture of {4-[4-(2-nitro-4-trifluoromethanesulfonyl-phenoxy)-benzenesulfonyl]-phenoxy}-acetic acid ethyl ester [Example 17, 61 mg, 0.1 mmol] in isopropanol (3.1 mL) and tetrahydrofuran (0.6 mL) was heated to reflux to dissolve all the solids. The mixture was cooled to 35° C. followed by addition of 1M NaOH solution (0.21 mL). It was then stirred at 35° C. for 2 hours. The reaction was concentrated, acidified with 1M HCl and extracted with ethyl acetate. The organic extracts were dried and concentrated to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ 12.2 (br s, 1H, COOH), 10.57 (s, 1H), 8.36 (d, J=2.6 Hz, 1H), 7.79 (m, 1H), 7.78 (d, J=9.0 Hz, 2H), 7.72 (d, J=8.8 Hz, 2H), 7.06 (d, J=9.0 Hz, 2H), 7.01 (d, J=9.3 Hz, 1H), 6.89 (d, J=8.8 Hz, 2H), 4.77 (s, 2H).

Workup

temperaturewas heated
temperatureto reflux
dissolutionto dissolve all the solids
concentrationThe reaction was concentrated
extractionextracted with ethyl acetate
customThe organic extracts were dried
concentrationconcentrated

Sources & evidence

ORD record: ord-beb79ce583194ea291c03533548e6300
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06596772B1

Reaction notes

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