Lithium Hydroxide → [4-(4-Dimethylsulfamoyl-benzoyl)-naphthalen-2-yl]-acetic acid

HRID 1644717Notes

Reaction equation

HRID 1644717 reaction equation
C([O:3][C:4](=[O:30])[CH2:5][C:6]1[CH:15]=[C:14]([C:16](=[O:29])[C:17]2[CH:22]=[CH:21][C:20]([S:23](=[O:28])(=[O:27])[N:24]([CH3:26])[CH3:25])=[CH:19][CH:18]=2)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1)C.[OH-].[Li+]>O1CCCC1.O>[CH3:26][N:24]([CH3:25])[S:23]([C:20]1[CH:19]=[CH:18][C:17]([C:16]([C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:7]=[C:6]([CH2:5][C:4]([OH:30])=[O:3])[CH:15]=2)=[O:29])=[CH:22][CH:21]=1)(=[O:27])=[O:28]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59350849[4-(4-Dimethylsulfamoyl-benzoyl)-naphthalen-2-yl]-acetic acid ethyl ester

Product 1

HCID 46204258[4-(4-Dimethylsulfamoyl-benzoyl)-naphthalen-2-yl]-acetic acidYield 77,878.5%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a stirred solution of [4-(4-dimethylsulfamoyl-benzoyl)-naphthalen-2-yl]-acetic acid ethyl ester (180 g, 0.42 mmol) in tetrahydrofuran:water (1:1; 4 mL) was added lithium hydroxide (40 mg, 0.97 mmol) at room temperature, and the resulting mixture was heated at reflux for 6 hours. The solvents were removed under reduced pressure, and the residue was washed with diethyl ether (5×5 mL), and then acidified with 50% aqueous hydrochloric acid solution (10 mL) and extracted with ethyl acetate (3×25 mL). The collected organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give a crude solid, which was further washed with a hexane/ethyl acetate/ether mixture and freeze dried to give pure [4-(4-dimethylsulfamoyl-benzoyl)-naphthalen-2-yl]-acetic acid (130 g, 77%) as a brown solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 12.35 (br. s, 1 H), 7.96-8.11 (m, 5 H), 7.91 (d, J=8.2 Hz, 2 H), 7.52-7.68 (m, 3 H), 3.83 (s, 2 H), 2.66 (s, 6 H); HRMS cald. for C21H19NO5S (ESI+) [(M+H)+] 398.1057, obsd. 398.1056.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 6 hours
  3. customThe solvents were removed under reduced pressure
  4. washthe residue was washed with diethyl ether (5×5 mL)
  5. extractionextracted with ethyl acetate (3×25 mL)
  6. dry with materialThe collected organic layers were dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a crude solid, which
  10. washwas further washed with a hexane/ethyl acetate/ether mixture and freeze
  11. customdried

Sources & evidence

ORD record
ord-802c688a5c7f42b981d10fb3d4bd5b72
Source dataset
uspto-grants-2012_02
Patent number
US08124629B2

Reaction notes

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