Trifluoroacetic acid → HCID 23511815, compound

HRID 350425Notes

Reaction equation

HRID 350425 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:26])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20]C(C)(C)C)=[O:19])=[CH:13][C:12]=1[CH3:25].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:26])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([OH:20])=[O:19])=[CH:13][C:12]=1[CH3:25]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23512004tert-butyl 4-[N'-(2-bromophenyl)ureido]-3-methylphenylacetate

Product 1

HCID 23511815HCID 23511815, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 4-[N′-(2-bromophenyl)ureido]-3-methylphenylacetate (1.27 g, 3.03 mmol) in CH2Cl2 (10 ml) was added TFA (5 ml) at room temperature. After 1 h stirring, the mixture was concentrated in vacuo. The residue was triturated by the addition of water, to give 4-[N′-(2-bromophenyl)ureido]-3-methylphenylacetic acid (1.05 g, 95%) as a pale yellow powder. mp 245–248° C. (dec.); 1 H-NMR (CDCl3) δ 2.24 (s, 3H), 3.48 (s, 2H), 6.96 (dt, J=7.3, 1.5 Hz, 1H), 7.02 (d, J=8.3 Hz, 1H), 7.07 (s, 1H), 7.32 (t, J=8.1 Hz, 1H), 7.59–7.66 (m, 2H), 8.44 (s, 1H), 8.62 (s, 1H); MS (ESI), m/z 363 (M++1), 365 (M++3); Anal. Calcd for C16H15BrN2O3.0.7H2O: C, 51.13; H, 4.40; Br, 21.26; N, 7.45. Found: C, 50.84; H, 4.62; Br, 21.72; N, 7.18.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customThe residue was triturated by the addition of water

Sources & evidence

ORD record
ord-c4c705fbedf6479588af557345621b22
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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