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Lithium hydroxide, monohydrate → [4-(4-Benzenesulfonylamino-phenyl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid

HRID 1468451
Notes
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Reaction equation

HRID 1468451 reaction equation
C[O:2][C:3](=[O:33])[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]=[CH:30][CH:29]=[CH:28][CH:27]=3)(=[O:25])=[O:24])=[CH:18][CH:17]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:32])[CH:11]=2)[CH:6]=1.O.[OH-].[Li+]>C1COCC1.O.CO.[OH-].[Na+]>[C:26]1([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:32])[CH:11]=4)[CH:6]=[C:5]([CH2:4][C:3]([OH:33])=[O:2])[C:14]=3[CH3:15])=[CH:21][CH:20]=2)(=[O:25])=[O:24])[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86695029[4-(4-Benzenesulfonylamino-phenyl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester

Product 1

HCID 71711646[4-(4-Benzenesulfonylamino-phenyl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acidYield 94.6%

Reagents, catalysts & solvents 4

HCID 887MethanolSolvent
HCID 962
Water
Solvent
HCID 8028TetrahydrofuranSolvent
HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of [4-(4-benzenesulfonylamino-phenyl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (38 mg, 0.08 mmol) in THF (2 mL) was added a solution of lithium hydroxide monohydrate (10 mg, 0.25 mmol) in water (1 mL) and methanol (1 mL) plus sodium hydroxide solution (1 ml, 1.0 N) at room temperature. The resulting clear solution was stirred for 4 h and then the solvents were removed under vacuum. The residue was diluted with water (10 mL). The mixture was 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 [4-(4-benzenesulfonylamino-phenyl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid (34 mg, 92%) as a light brown foam. 1H NMR (300 MHz, DMSO-d6) δ ppm 12.43 (br. s, 1 H), 10.44 (s, 1 H), 7.88-8.02 (m, 1 H), 7.76-7.87 (m, 3 H), 7.50-7.71 (m, 3 H), 7.33 (t, J=7.7 Hz, 1 H), 7.24 (d, J=8.0 Hz, 2 H), 7.09 (d, J=8.0 Hz, 2 H), 6.58 (d, J=11.2 Hz, 1 H), 3.80 (br. s, 2 H), 2.00 (s, 3 H). HRMS calcd. for C25H19FNO4S [(M−H)−] 448.1024, obsd. 448.1022.

Workup

  1. customthe 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-d8d6ec7517dd41eb9350f283fc773d7f
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09000044B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes