Trifluoroacetic acid → HCID 23512271, compound

HRID 350402Notes

Reaction equation

HRID 350402 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:34])[NH:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]([O:27]C(C)(C)C)=[O:26])=[CH:20][C:19]=1[O:32][CH3:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:34])[NH:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]([OH:27])=[O:26])=[CH:20][C:19]=1[O:32][CH3:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23511829HCID 23511829, compound

Product 1

HCID 23512271HCID 23512271, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-[N′-(2-benzyloxyphenyl)ureido]-3-methoxyphenylacetate (2.35 g, 5.08 mmol) in CH2Cl2 (25 mL) was added TFA (25 mL) at 0° C. After being stirred at room temperature for 3 hr, the mixture was concentrated. The residue was dissolved in 1 N NaOH and washed with Et2O. The basic water layer was poured into ice-1 N HCl and the resulting mixture was extracted with CHCl3-MeOH (4:1, v/v). The extracts were washed with brine, dried over Na2SO4, and concentrated to dryness. The residue was dissolved in isopropyl ether and hexane was added to this solution until the crystallization was completed. The solid was collected to give 4-[N′-(2-benzyloxyphenyl)ureido]-3-methoxyphenylacetic acid (1.59 g, 77%) as a brownish solid. 1H-NMR (DMSO-d6) δ 3.50 (s, 2H), 3.85 (s, 3H), 5.26 (s, 2H), 6.76 (d, J=8.3 Hz, 1H), 6.83–6.89 (m, 2H), 6.91 (s, 1H), 7.01 (dd, J=8.3, 2.3 Hz, 1H), 7.31 (t, J=7.3 Hz, 1H), 7.39 (t, J=7.3 Hz, 2H), 7.49 (d, J=7.3 Hz, 2H), 7.97 (d, J=8.3 Hz, 1H), 8.04 (d, J=8.3 Hz, 1H), 8.80 (s, 1H), 8.86 (s, 1H), 12.24 (broad s, 1H); FAB-MS m/z 407 (M++1).

Workup

  1. concentrationthe mixture was concentrated
  2. dissolutionThe residue was dissolved in 1 N NaOH
  3. washwashed with Et2O
  4. additionThe basic water layer was poured into ice-1 N HCl
  5. extractionthe resulting mixture was extracted with CHCl3-MeOH (4:1
  6. washThe extracts were washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated to dryness
  9. dissolutionThe residue was dissolved in isopropyl ether
  10. additionhexane was added to this solution until the crystallization
  11. customThe solid was collected

Sources & evidence

ORD record
ord-f774aac25fba454ca19483d8a1ca434b
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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