Trifluoroacetic acid → HCID 60198585, compound

HRID 133426Notes

Reaction equation

HRID 133426 reaction equation
C([O:5][C:6]([CH:8]([NH:12][S:13]([C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][C:25]([O:28][C:29]([C:31]3[O:32][C:33]4[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=4[CH:35]=3)=[O:30])=[CH:24][CH:23]=2)=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH:9]([CH3:11])[CH3:10])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[C:6]([CH:8]([NH:12][S:13]([C:16]1[CH:17]=[CH:18][C:19]([C:22]2[CH:27]=[CH:26][C:25]([O:28][C:29]([C:31]3[O:32][C:33]4[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=4[CH:35]=3)=[O:30])=[CH:24][CH:23]=2)=[CH:20][CH:21]=1)(=[O:14])=[O:15])[CH:9]([CH3:11])[CH3:10])([OH:7])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67109825Benzofuran-2-carboxylic acid 4'-(1-tert-butoxycarbonyl-2-methyl-propylsulfamoyl)-biphenyl-4-yl ester

Product 1

HCID 60198585HCID 60198585, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzofuran-2-carboxylic acid 4′-(1-tert-butoxycarbonyl-2-methyl-propylsulfamoyl)-biphenyl-4-yl ester (325 mg) was dissolved in dichloromethane (15 mL) and added with TFA. The solution was stirred at room temperature for 7 hrs. Solvent was removed by rotovap and crude product purified by column chromatography (5-20% MeOH/EtOAc) to yield Benzofuran-2-carboxylic acid 4′-(1-carboxy-2-methyl-propylsulfamoyl)-biphenyl-4-yl ester in 76% yield (241 mg).

Workup

  1. customSolvent was removed by rotovap and crude product
  2. custompurified by column chromatography (5-20% MeOH/EtOAc)

Sources & evidence

ORD record
ord-c201a21021874c73ac97b4d4634825cf
Source dataset
uspto-grants-2008_06
Patent number
US07390833B2

Reaction notes

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