Lithium Hydroxide → HCID 25263394, compound

HRID 1162528Notes

Reaction equation

HRID 1162528 reaction equation
C[O:2][C:3](=[O:38])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:16]([C:17](=[O:30])[NH:18][CH2:19][CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=3[Cl:29])=[C:15]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[O:14][N:13]=2)=[CH:8][C:7]=1[CH3:37].[Li+].[OH-]>COCCOC.O>[Cl:29][C:23]1[CH:24]=[C:25]([Cl:28])[CH:26]=[CH:27][C:22]=1[O:21][CH2:20][CH2:19][NH:18][C:17]([C:16]1[C:12]([C:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:4][C:3]([OH:38])=[O:2])=[C:7]([CH3:37])[CH:8]=2)=[N:13][O:14][C:15]=1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:30]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68647972HCID 68647972, compound

Product 1

HCID 25263394HCID 25263394, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

The crude (4-{4-[2-(2,4-dichloro-phenoxy)-ethyl-carbamoyl]-5-phenyl-isoxazol-3-yl}-2-methyl-phenoxy)-acetic acid methyl ester is dissolved in DME (1 mL). A solution of 1 M LiOH in H2O (0.2 mL) and is added and the mixture is stirred overnight at room temperature. The mixture is concentrated, then acidified with 1 M HCl, extracted with EtOAc (10 mL), dried over MgSO4, filtered, concentrated and purified on reverse phase HPLC (H2O/MeCN gradient) to afford the title compound I30 as a white solid: 1H-NMR (400 MHz, CD3CN) δ=7.56 (d, J=1.6, 1H), 7.49 (dd, J=8.4, 2.4 Hz, 1H), 7.45 (m, 5H), 7.39 (d, J=2.4 Hz, 1H), 7.27 (dd, J=8.8, 2.8 Hz, 1H), 7.20 (t, J=5.6 Hz, NH), 6.96 (d, J=8.8 Hz, 1H), 6.73 (d, J=8.8 Hz, 1H), 4.64 (s, 2H), 4.08 (t, J=5.2 Hz, 2H), 3.70 (q, J=5.3 Hz, 2H), 2.23 (s, 3H). MS calculated for C27H23Cl2N2O6 (M+H+) 541.0, found 541.0.

Workup

  1. concentrationThe mixture is concentrated
  2. extractionextracted with EtOAc (10 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified on reverse phase HPLC (H2O/MeCN gradient)

Sources & evidence

ORD record
ord-3d29dd3954884549ada121b4635bf049
Source dataset
uspto-grants-2010_10
Patent number
US07820705B2

Reaction notes

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