Hydrochloric Acid → HCID 11497604, compound

HRID 1162520Notes

Reaction equation

HRID 1162520 reaction equation
C[O:2][C:3](=[O:37])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]([C:16](=[O:29])[NH:17][CH2:18][CH2:19][O:20][C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=3[Cl:28])=[C:14]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[O:13][N:12]=2)=[C:7]([Cl:36])[CH:6]=1.[Li+].[OH-].Cl.C(Cl)Cl>C1COCC1.O>[Cl:36][C:7]1[CH:6]=[C:5]([CH2:4][C:3]([OH:37])=[O:2])[CH:10]=[CH:9][C:8]=1[C:11]1[C:15]([C:16](=[O:29])[NH:17][CH2:18][CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[Cl:28])=[C:14]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[O:13][N:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 6344DichloromethaneHCID 59520433HCID 59520433, compound

Product 1

HCID 11497604HCID 11497604, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The crude (3-Chloro-4-{4-[2-(2,4-dichloro-phenoxy)-ethylcarbamoyl]-5-phenyl-isoxazol-3-yl}-phenyl)-acetic acid methyl ester 36 (0.85 mmol) is dissolved in THF (5 mL). A solution of 1 M LiOH in H2O (2 mL) is added and the mixture is stirred overnight at room temperature. The mixture is acidified with 1 M HCl (3 mL), DCM (50 mL) is added and the organic layer washed with H2O (3×30 mL). The organic layer is dried (MgSO4), filtered, concentrated and purified on reverse phase HPLC (H2O/MeCN gradient) to afford the title compound G1 as a white solid: 1H-NMR (400 MHz, CDCl3) δ=7.93 (dd, J=1.8 Hz, J=7.8 Hz, 2H), 7.52-7.23 (m, 7H), 7.17 (dd, J=8.8 Hz, J=2.5 Hz, 1H), 6.71 (d, J=8.8 Hz, 1H), 6.15 (t, J=5.3 Hz, NH), 3.92 (t, J=4.8 Hz, 2H), 3.72 (q, J=5.3 Hz, 2H), 3.50 (s, 2H). MS calculated for C26H20Cl3N2O5 (M+H+) 545.0, found 545.3.

Workup

  1. additionis added
  2. washthe organic layer washed with H2O (3×30 mL)
  3. dry with materialThe organic layer is dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified on reverse phase HPLC (H2O/MeCN gradient)

Sources & evidence

ORD record
ord-0112a59181d240e19b8306d7695f8cf7
Source dataset
uspto-grants-2010_10
Patent number
US07820705B2

Reaction notes

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