Trifluoroacetic acid → HCID 46935553, compound

HRID 1626729Notes

Reaction equation

HRID 1626729 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([C:12]([NH:14][C:15]3[S:16][C:17]([CH3:33])=[C:18]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:19]=3[C:20]([O:22]C(C)(C)C)=[O:21])=[O:13])[CH:9]=[CH:10][CH:11]=2)=[CH:2]1.FC(F)(F)C(O)=O.CCCCCC>C(Cl)(Cl)Cl>[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([C:12]([NH:14][C:15]3[S:16][C:17]([CH3:33])=[C:18]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[C:19]=3[C:20]([OH:22])=[O:21])=[O:13])[CH:9]=[CH:10][CH:11]=2)=[CH:2]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8058HexaneHCID 66681163HCID 66681163, compound

Product 1

HCID 46935553HCID 46935553, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

0.5 g (1.2 mmol) of tert-butyl 2-({[3-(furan-3-yl)phenyl]carbonyl}amino)-5-methyl-4-phenylthiophene-3-carboxylate was dissolved in 2 mL of chloroform, and 5 mL of trifluoroacetic acid (TFA) was added thereto at 0° C. The mixture was stirred at room temperature for 5 hours. n-hexane was added to the reaction mixture, and solids were collected by filtration, followed by recrystallization using a mixed solvent of ethyl acetate and n-hexane, thereby giving 0.34 g of the target 2-({[3-(furan-3-yl)phenyl]carbonyl}amino)-5-methyl-4-phenylthiophene-3-carboxylic acid (yield: 70%).

Workup

  1. customat 0° C
  2. filtrationwere collected by filtration
  3. customfollowed by recrystallization

Sources & evidence

ORD record
ord-fe5d13e28d4e4d7b88db4fafaa251322
Source dataset
uspto-grants-2014_07
Patent number
US08785473B2

Reaction notes

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