Sodium Hydroxide → {4-[4-(3,5-Bis-trifluoromethyl-benzenesulfonylamino)-phenyl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid

HRID 1468453Notes

Reaction equation

HRID 1468453 reaction equation
C[O:2][C:3](=[O:41])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][S:23]([C:26]3[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[C:28]([C:36]([F:39])([F:38])[F:37])[CH:27]=3)(=[O:25])=[O:24])=[CH:18][CH:17]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:40])[CH:11]=2)[CH:6]=1.[OH-].[Na+]>C(O)C>[F:35][C:32]([F:33])([F:34])[C:30]1[CH:31]=[C:26]([S:23]([NH:22][C:19]2[CH:18]=[CH:17][C:16]([C:13]3[C:12]4[C:7](=[CH:8][CH:9]=[C:10]([F:40])[CH:11]=4)[CH:6]=[C:5]([CH2:4][C:3]([OH:41])=[O:2])[C:14]=3[CH3:15])=[CH:21][CH:20]=2)(=[O:25])=[O:24])[CH:27]=[C:28]([C:36]([F:38])([F:39])[F:37])[CH:29]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86695030{4-[4-(3,5-Bis-trifluoromethyl-benzenesulfonylamino)-phenyl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid methyl ester

Product 1

HCID 71711645{4-[4-(3,5-Bis-trifluoromethyl-benzenesulfonylamino)-phenyl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acidYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of {4-[4-(3,5-bis-trifluoromethyl-benzenesulfonylamino)-phenyl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (21 mg, 0.035 mmol) in ethanol (2 mL) was added sodium hydroxide solution (105 uL, 1.0 N,) at room temperature. The resulting clear solution was stirred for 4 h. Then, the solvents were removed under vacuum and the residue was diluted with water (10 mL), acidified with 1.0 N hydrochloric acid, extracted with ethyl acetate (2×20 mL). The combined organic extracts were washed with brine solution (20 mL) and dried over anhydrous magnesium sulfate. Filtration of the drying agent and concentration of the solvent under vacuum provided the desired {4-[4-(3,5-bis-trifluoromethyl-benzenesulfonylamino)-phenyl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid (17 mg, 83%) as a light brown foam. 1H NMR (300 MHz, DMSO-d6) δ ppm 12.45 (br. s, 1 H), 10.59 (br. s, 1 H), 8.53 (br. s, 1 H), 8.21 (s, 2 H), 7.89-8.03 (m, 1 H), 7.83 (s, 1 H), 7.34 (t, J=8.2 Hz, 1 H), 7.25 (d, J=7.5 Hz, 2 H), 7.16 (d, J=7.8 Hz, 2 H), 6.59 (d, J=11.2 Hz, 1 H), 3.81 (br. s, 2 H), 1.98 (s, 3 H). HRMS calcd. for C27H17F7NO4S [(M−H)−] 584.0772, obsd. 584.0771.

Workup

  1. customThen, the solvents were removed under vacuum
  2. additionthe residue was diluted with water (10 mL)
  3. extractionextracted with ethyl acetate (2×20 mL)
  4. washThe combined organic extracts were washed with brine solution (20 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationFiltration of the drying agent and concentration of the solvent under vacuum

Sources & evidence

ORD record
ord-e5da95c388534f7c91643b14a9da4de7
Source dataset
uspto-grants-2015_04
Patent number
US09000044B2

Reaction notes

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