Hydrochloric Acid → HCID 44414901, compound

HRID 1162523Notes

Reaction equation

HRID 1162523 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])NCCOC3C=CC(Cl)=CC=3Cl)=[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-:39].[ClH:40].[CH2:41]([Cl:43])Cl>C1COCC1.O>[Cl:36][C:7]1[CH:6]=[C:5]([CH2:4][C:3]([OH:2])=[O:37])[CH:10]=[CH:9][C:8]=1[C:11]1[C:15]([C:16](=[O:29])[CH2:9][CH2:8][CH2:11][O:39][C:7]2[CH:6]=[CH:5][C:4]([Cl:40])=[CH:3][C:41]=2[Cl:43])=[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 44414901HCID 44414901, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Crude (3-Chloro-4-{4-[2-(2,4-dichloro-phenoxy)-ethylcarbamoyl]-5-phenyl-isoxazol-3-yl}-phenyl)-acetic acid methyl ester 45 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 h 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 (minor isomer!): 1H-NMR (400 MHz, CDCl3) δ=7.65 (d, J=7.0 Hz, 2H), 7.39-6.93 (m, 8H), 6.54 (d, J=8.8 Hz, 1H), 3.72 (t, J=5.9 Hz, 2H), 3.53 (s, 2H), 2.50 (t, J=6.8 Hz, 2H), 1.88 (m, 2H). MS calculated for C27H21Cl3NO5 (M+H+) 544.0, found 544.1.

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-d0ec8a6859af459e995147f02adf88c7
Source dataset
uspto-grants-2010_10
Patent number
US07820705B2

Reaction notes

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