Trifluoroacetic acid → 2-(4-(4-((2,4-Dichlorophenethyl)carbamoyl)-3-fluorophenoxy)-3-cyanophenyl)acetic acid

HRID 1927789Notes

Reaction equation

HRID 1927789 reaction equation
[Cl:1][C:2]1[CH:36]=[C:35]([Cl:37])[CH:34]=[CH:33][C:3]=1[CH2:4][CH2:5][NH:6][C:7]([C:9]1[CH:31]=[CH:30][C:12]([O:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23]C(C)(C)C)=[O:22])=[CH:16][C:15]=2[C:28]#[N:29])=[CH:11][C:10]=1[F:32])=[O:8].C(O)(C(F)(F)F)=O>ClCCl>[Cl:1][C:2]1[CH:36]=[C:35]([Cl:37])[CH:34]=[CH:33][C:3]=1[CH2:4][CH2:5][NH:6][C:7]([C:9]1[CH:31]=[CH:30][C:12]([O:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]([OH:23])=[O:22])=[CH:16][C:15]=2[C:28]#[N:29])=[CH:11][C:10]=1[F:32])=[O:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68468374Tert-butyl 2-(4-(4-((2,4-dichlorophenethyl)carbamoyl)-3-fluorophenoxy)-3-cyanophenyl)acetate

Product 1

HCID 594031982-(4-(4-((2,4-Dichlorophenethyl)carbamoyl)-3-fluorophenoxy)-3-cyanophenyl)acetic acidYield 31.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 2-(4-(4-((2,4-dichlorophenethyl)carbamoyl)-3-fluorophenoxy)-3-cyanophenyl)acetate (15 mg, 0.0276 mmol) in dichloromethane was added TFA. The reaction was stirred for 2 hours and then concentrated. The crude material was purified by preparative TLC (10% methanol/0.5% AcOH/dichloromethane). The appropriate section was collected and then purified a second time by preparative TLC to provide 2-(4-(4-((2,4-dichlorophenethyl)carbamoyl)-3-fluorophenoxy)-3-cyanophenyl)acetic acid (0.0042 g). 1H NMR (400 MHz, CD3OD) δ 7.70-7.74 (m, 2H), 7.61 (d, J=7.8 Hz, 1H), 7.43 (s, 1H), 7.33 (d, J=8.6 Hz, 1H), 7.26 (d, J=7.8 Hz, 1H), 7.13 (d, J=8.7 Hz, 1H), 6.88-6.94 (m, 2H), 3.52-3.65 (m, 4H), 3.05 (t, J=7.0 Hz, 2H).

Workup

  1. concentrationconcentrated
  2. customThe crude material was purified by preparative TLC (10% methanol/0.5% AcOH/dichloromethane)
  3. customThe appropriate section was collected
  4. custompurified a second time by preparative TLC

Sources & evidence

ORD record
ord-36f8cafbbf9847459195ad38512043f7
Source dataset
uspto-grants-2012_05
Patent number
US08183289B2

Reaction notes

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