Hydrochloric Acid → HCID 44414900, compound

HRID 1162522Notes

Reaction equation

HRID 1162522 reaction equation
C[O:2][C:3](=[O:36])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]([CH2:16][O: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:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[O:13][N:12]=2)=[C:7]([Cl:35])[CH:6]=1.[Li+].[OH-].Cl.C(Cl)Cl>C1COCC1.O>[Cl:35][C:7]1[CH:6]=[C:5]([CH2:4][C:3]([OH:36])=[O:2])[CH:10]=[CH:9][C:8]=1[C:11]1[C:15]([CH2:16][O: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:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[O:13][N:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 6344DichloromethaneHCID 68647916HCID 68647916, compound

Product 1

HCID 44414900HCID 44414900, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(3-Chloro-4-{4-[2-(2,4-dichloro-phenoxy)-ethoxymethyl]-5-phenyl-isoxazol-3-yl}-phenyl)-acetic acid methyl ester 41 (0.75 mmol) is dissolved in THF (5 mL). A solution of 1 M LiOH in H2O (3.5 mL) is added and the mixture is stirred for 6 hours 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 (2×30 mL). The organic layer is dried (MgSO4), filtered, concentrated and purified on reverse phase HPLC (H2O/MeCN gradient) to afford the title compound H2 as a white solid: 1H-NMR (400 MHz, CDCl3) δ=7.84 (m, 2H), 7.44-7.19 (m, 7H), 7.06 (dd, J=8.8 Hz, J=2.5 Hz, 1H), 6.70 (d, J=8.8 Hz, 1H), 4.45 (s, 2H), 4.00 (t, J=4.5 Hz, 2H), 3.71 (t, J=4.5 Hz, 2H), 3.62 (s, 2H). MS calculated for C26H21Cl3NO5 (M+H+) 532.0, found 532.1.

Workup

  1. additionis added
  2. washthe organic layer washed with H2O (2×30 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-95760aaa7f58475a9e6e0b8714fea5b3
Source dataset
uspto-grants-2010_10
Patent number
US07820705B2

Reaction notes

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