Hydrochloric Acid → N-Benzyl-N-(2-benzyloxy-5-hydroxy-phenyl)-benzenesulfonamide

HRID 1061209Notes

Reaction equation

HRID 1061209 reaction equation
[C:1]1([S:7]([N:10]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:11]2[CH:12]=[C:13]([O:25]C(=O)C3C=CC=CC=3)[CH:14]=[CH:15][C:16]=2[O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl>C1COCC1.CO.O>[CH2:34]([N:10]([C:11]1[CH:12]=[C:13]([OH:25])[CH:14]=[CH:15][C:16]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[S:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:9])=[O:8])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86584544Benzoic acid 3-(benzenesulfonyl-benzyl-amino)-4-benzyloxy-phenyl ester

Product 1

HCID 22220539N-Benzyl-N-(2-benzyloxy-5-hydroxy-phenyl)-benzenesulfonamideYield 82.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of benzoic acid 3-(benzenesulfonyl-benzyl-amino)-4-benzyloxy-phenyl ester (which was obtained in Example 18) (1.80 g, 3.28 mmol) in THF (10 mL) and methanol (10 mL) was added 10% of sodium hydroxide (10 mL). The mixture was stirred at room temperature for 1.5 hours, acidified with concentrated hydrochloric acid and diluted with water (200 mL). The aqueous solution was extracted with CH2Cl2. The organic phase was dried over MgSO4 and concentrated. The product was purified by flash silica gel chromatography eluting with ethyl acetate and hexanes to give the title compound as a white solid (1.20 g, 82%); 1H NMR (300 MHz, CDCl3) δ 4.71 (brs, 4H), 6.49 (d, J=3.0 Hz, 1H), 6.62(dd, J=9.0, 3.0 Hz, 1H), 6.84 (d, J=9.0 Hz, 1H), 7.10-7.70 (m, 15H), 9.07 (brs, 1H); MS (ES) m/z: 444.0 ((M−H)−, 100%); HRMS Calcd. for C26H22NO4S(M−H)−: 444.1275. Found: 444.1270.

Workup

  1. extractionThe aqueous solution was extracted with CH2Cl2
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated
  4. customThe product was purified by flash silica gel chromatography
  5. washeluting with ethyl acetate and hexanes

Sources & evidence

ORD record
ord-6fda2c8b8198495aacca7e5e58c3f311
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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