Benzyl Chloride → Benzoic acid 3-(benzenesulfonyl-benzyl-amino)-4-benzyloxy-phenyl ester

HRID 1061208Notes

Reaction equation

HRID 1061208 reaction equation
[C:1]1([S:7]([NH:10][C:11]2[CH:12]=[C:13]([O:25][C:26](=[O:33])[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=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.[H-].[Na+].[H][H].[CH2:38](Cl)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>CN(C=O)C>[C:1]1([S:7]([N:10]([CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:11]2[CH:12]=[C:13]([O:25][C:26](=[O:33])[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=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:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 86584543Benzoic acid 3-benzenesulfonylamino-4-benzyloxy-phenyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 86584544Benzoic acid 3-(benzenesulfonyl-benzyl-amino)-4-benzyloxy-phenyl esterYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

To a stirred solution of benzoic acid 3-benzenesulfonylamino-4-benzyloxy-phenyl ester (which was obtained in Example 17) (2.88 g, 7.27 mmol) in DMF (20 mL) was added 60% sodium hydride (0.32 g, 8 mmol). After hydrogen evolution had subsided the stirred mixture was heated at 70° C. for 15 minute, and then it was cooled down to room temperature and a solution of benzyl chloride (1.01 g, 8 mmol) in 5 mL of DMF was added dropwise. The mixture was then heated at 85-90° C. for 2 hours, then it was cooled down to room temperature, poured into ice-water. The aqueous layer was extracted with ethyl acetate and the organic layer was dried 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 (2.40 g, 70%); 1H NMR (300 MHz, CDCl3) δ 4.74 (s, 2H), 4.83 (s, 2H), 8.83 (d, J=8.9 Hz, 1H), 8.10-8.50 (m, 2H); HRMS Calcd. for C33H28NO5S(MH+): 550.1688. Found: 550.1680.

Workup

  1. temperatureit was cooled down to room temperature
  2. temperatureThe mixture was then heated at 85-90° C. for 2 hours
  3. temperatureit was cooled down to room temperature
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. customthe organic layer was dried
  6. concentrationconcentrated
  7. customThe product was purified by flash silica gel chromatography
  8. washeluting with ethyl acetate and hexanes

Sources & evidence

ORD record
ord-0d673932e26a4f948b236b5dbb469526
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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