Trifluoroacetic acid → HCID 59403197, compound

HRID 453507Notes

Reaction equation

HRID 453507 reaction equation
[Cl:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:31]=[CH:30][C:14]([O:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C:23]([O:25]C(C)(C)C)=[O:24])=[CH:18][CH:17]=3)=[CH:13][CH:12]=2)=[O:10])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:12]=[CH:13][C:14]([O:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C:23]([OH:25])=[O:24])=[CH:18][CH:17]=3)=[CH:30][CH:31]=2)=[O:10])=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68465652HCID 68465652, compound

Product 1

HCID 59403197HCID 59403197, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)phenyl)acetate (20 mg, 0.043 mmol) was diluted with DCM (1 mL) followed by the addition of TFA (1 mL). After stirring for 2 hours, the reaction was concentrated, diluted with ether and concentrated to yield 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)phenyl)acetic acid (17 mg, 97% yield) as a white solid. 1H NMR (400 MHz, CD3Cl3, CD3OD) 7.70 (d, 2H), 7.30 (m, 4H), 7.19 (m, 2H), 7.00 (m, 4H), 3.62 (m, 4H), 2.90 (t, 2H).

Workup

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

Sources & evidence

ORD record
ord-354aa25df5c243daa1e8cb08e4d4cfbd
Source dataset
uspto-grants-2013_07
Patent number
US08492437B2

Reaction notes

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