4-(4'-Methoxy-biphenyl-4-yloxymethyl)-5-methyl-furan-2-carboxylic acid → 4-Hydroxy-N-[4-(4'-methoxy-biphenyl-4-yloxymethyl)-5-methyl-furan-2-carbonyl]-benzenesulfonamide

HRID 490334Notes

Reaction equation

HRID 490334 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]3[CH:18]=[C:19]([C:23](O)=[O:24])[O:20][C:21]=3[CH3:22])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[S:26]([C:30]1[CH:35]=[CH:34][C:33]([O:36]C(=O)C)=[CH:32][CH:31]=1)(=[O:29])(=[O:28])[NH2:27].C[O-].[Na+]>CO.O>[OH:36][C:33]1[CH:34]=[CH:35][C:30]([S:26]([NH:27][C:23]([C:19]2[O:20][C:21]([CH3:22])=[C:17]([CH2:16][O:15][C:12]3[CH:11]=[CH:10][C:9]([C:6]4[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)=[CH:14][CH:13]=3)[CH:18]=2)=[O:24])(=[O:28])=[O:29])=[CH:31][CH:32]=1

Participants

6

Reactant 3

HCID 104272364-(4'-Methoxy-biphenyl-4-yloxymethyl)-5-methyl-furan-2-carboxylic acidHCID 10942334Sodium MethoxideHCID 597731074-Sulfamoylphenyl acetate

Product 1

HCID 184445964-Hydroxy-N-[4-(4'-methoxy-biphenyl-4-yloxymethyl)-5-methyl-furan-2-carbonyl]-benzenesulfonamideYield 20.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

4-(4′-Methoxy-biphenyl-4-yloxymethyl)-5-methyl-furan-2-carboxylic acid (4) (50 mg) was reacted with acetic acid 4-sulphamoyl-phenyl ester (64 mg) in an analogous manner to that described in Example 2A. The acetic ester intermediate was hydrolysed with sodium methoxide (80 mg) in a mixture of methanol (10 mL) and water (1 mL) for 1 hour. The solution was concentrated in vacuo then partitioned between dichloromethane (10 mL) and water (10 mL). The organic layer was washed with brine (10 mL), dried, filtered and concentrated in vacuo. The crude product was purified by preparative HPLC (starting at 30% acetonitrile and increasing at a rate of 1% per minute up to 98% acetonitrile) to give compound 13 as a white solid (15 mg). LC/MS System C: Rt=3.50 mins, m/z (ES−)=492 (M− for C26H23N2O7S).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthen partitioned between dichloromethane (10 mL) and water (10 mL)
  3. washThe organic layer was washed with brine (10 mL)
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by preparative HPLC (
  8. temperatureincreasing at a rate of 1% per minute up to 98% acetonitrile)

Sources & evidence

ORD record
ord-713b3d2eb17e48deb51b781b92f7bfae
Source dataset
uspto-grants-2009_05
Patent number
US07528157B2

Reaction notes

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