Trifluoroacetic acid → 2-(4-(4-((3,4-Dichlorophenyl)carbamoyl)phenoxy)-3-(methylsulfonamidomethyl)phenyl)acetic acid

HRID 1927726Notes

Reaction equation

HRID 1927726 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[CH:38]=[CH:37][C:15]([O:16][C:17]3[CH:22]=[CH:21][C:20]([CH2:23][C:24]([O:26]C(C)(C)C)=[O:25])=[CH:19][C:18]=3[CH2:31][NH:32][S:33]([CH3:36])(=[O:35])=[O:34])=[CH:14][CH:13]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[CH:13]=[CH:14][C:15]([O:16][C:17]3[CH:22]=[CH:21][C:20]([CH2:23][C:24]([OH:26])=[O:25])=[CH:19][C:18]=3[CH2:31][NH:32][S:33]([CH3:36])(=[O:35])=[O:34])=[CH:37][CH:38]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68463349Tert-butyl 2-(4-(4-((3,4-dichlorophenyl)carbamoyl)phenoxy)-3-(methylsulfonamidomethyl)phenyl)acetate

Product 1

HCID 248225232-(4-(4-((3,4-Dichlorophenyl)carbamoyl)phenoxy)-3-(methylsulfonamidomethyl)phenyl)acetic acidYield 75.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of step E (22 mg, 0.038 mmol) was diluted with methylene chloride (1 mL) followed by the addition of TFA (1 mL). After stirring for 1 hour, the reaction was concentrated, diluted with ether, sonicated and concentrated to yield 2-(4-(4-((3,4-dichlorophenyl)carbamoyl)phenoxy)-3-(methylsulfonamidomethyl)phenyl)acetic acid (15 mg, 75% yield) as a white solid. 1H NMR (400 MHz, CDCl3/CD3OD) 7.92 (m, 1H), 7.90 (d, 2H), 7.59 (m, 1H), 7.42 (m, 2H), 7.25 (m, 1H), 7.10 (d, 2H), 6.90 (d, 1H), 4.28 (s, 2H), 3.62 (s, 2H), 2.85 (s, 3H).

Workup

  1. concentrationthe reaction was concentrated
  2. additiondiluted with ether
  3. customsonicated
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1140afed7d534d24a47b28f059ffaabf
Source dataset
uspto-grants-2012_05
Patent number
US08183289B2

Reaction notes

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