Sodium Hydroxide → {6-Chloro-3-methyl-4-[4-(toluene-2-sulfonylamino)-phenyl]-naphthalen-2-yl}-acetic acid

HRID 1468458Notes

Reaction equation

HRID 1468458 reaction equation
C[O:2][C:3](=[O:34])[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[C:27]([CH3:32])=[CH:28][CH:29]=[CH:30][CH:31]=3)(=[O:25])=[O:24])=[CH:18][CH:17]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:33])[CH:11]=2)[CH:6]=1.[OH-].[Na+]>C(O)C>[Cl:33][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[CH:6]=[C:5]([CH2:4][C:3]([OH:34])=[O:2])[C:14]([CH3:15])=[C:13]2[C:16]1[CH:17]=[CH:18][C:19]([NH:22][S:23]([C:26]2[C:27]([CH3:32])=[CH:28][CH:29]=[CH:30][CH:31]=2)(=[O:24])=[O:25])=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86695033{6-Chloro-3-methyl-4-[4-(toluene-2-sulfonylamino)-phenyl]-naphthalen-2-yl}-acetic acid methyl ester

Product 1

HCID 71711712{6-Chloro-3-methyl-4-[4-(toluene-2-sulfonylamino)-phenyl]-naphthalen-2-yl}-acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of {6-chloro-3-methyl-4-[4-(toluene-2-sulfonylamino)-phenyl]-naphthalen-2-yl}-acetic acid methyl ester (85 mg, 0.17 mmol) in ethanol (7 mL) was added a solution of sodium hydroxide solution (516 uL, 1.0 N) at room temperature. The resulting clear solution was stirred overnight. Then, the solvents were removed under vacuum and the residue was diluted with water (10 mL), acidified with 1.0 N hydrochloric acid, and 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 {6-chloro-3-methyl-4-[4-(toluene-2-sulfonylamino)-phenyl]-naphthalen-2-yl}-acetic acid as a light brown foam. 1H NMR (300 MHz, DMSO-d6) δ ppm 12.44 (br. s, 1 H), 10.54 (br. s, 1 H), 7.88-7.95 (m, 2 H), 7.82 (s, 1 H), 7.48-7.58 (m, 1 H), 7.35-7.46 (m, 3 H), 7.22 (d, J=8.5 Hz, 2 H), 7.08 (d, J=8.5 Hz, 2 H), 6.92 (d, J=1.5 Hz, 1 H), 3.80 (s, 2 H), 2.63 (s, 3 H), 1.99 (s, 3 H). HRMS calcd. for C26H21ClNO4S [(M−H)−] 478.0885, obsd. 478.0885.

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-2d63567f93e845a2852e901366476dde
Source dataset
uspto-grants-2015_04
Patent number
US09000044B2

Reaction notes

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