Sodium Hydroxide → 4-((4-hydroxy-N-(2-methoxybenzyl)phenylsulfonamido)methyl)-benzoic acid

HRID 1770479Notes

Reaction equation

HRID 1770479 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]([CH2:24][C:25]2[CH:34]=[CH:33][C:28]([C:29]([O:31]C)=[O:30])=[CH:27][CH:26]=2)[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH3:23])(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=O)C.[OH-].[Na+]>C1COCC1>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([S:11]([N:14]([CH2:24][C:25]2[CH:26]=[CH:27][C:28]([C:29]([OH:31])=[O:30])=[CH:33][CH:34]=2)[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH3:23])(=[O:12])=[O:13])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66974740methyl 4-((4-acetoxy-N-(2-methoxybenzyl)phenylsulfonamido)methyl)benzoate

Product 1

HCID 252072894-((4-hydroxy-N-(2-methoxybenzyl)phenylsulfonamido)methyl)-benzoic acidYield 15%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-((4-acetoxy-N-(2-methoxybenzyl)phenylsulfonamido)methyl)benzoate (crude) was dissolved in THF (1.0 mL) and treated with aqueous NaOH (1N, 2.0 mL, 2.0 mmol). The mixture was refluxed for an hour. Upon completion the THF was removed in vacuo and the resulting aqueous solution was acidified with 6 N aq HCl to a pH of ˜3. The aqueous phase was extracted with EtOAc (2×15 mL) and the combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated. The crude product was purified by reverse phase HPLC to afford 10.8 mg of the title compound (15% yield over two steps). MS (M−H, 426.1); 1H NMR (400 MHz, acetone-d6): δ, ppm: 3.65 (s, 3H), 4.37 (s, 2H), 4.43 (s, 2H), 6.79 (m, 2H), 7.01 (d, 2H, J=8.0 Hz), 7.17 (m, 2H), 7.28 (d, 2H, J=7.9 Hz), 7.73 (d, 2H, J=8.0 Hz), 7.87 (d, 2H, J=7.9 Hz).

Workup

  1. temperatureThe mixture was refluxed for an hour
  2. customUpon completion the THF was removed in vacuo
  3. extractionThe aqueous phase was extracted with EtOAc (2×15 mL)
  4. washthe combined organic layers were washed with water, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-a65932fbd915448ba060589b573f0b9c
Source dataset
uspto-grants-2016_02
Patent number
US09247759B2

Reaction notes

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