Lithium Hydroxide → HCID 10256736, compound

HRID 2251322Notes

Reaction equation

HRID 2251322 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:13]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]([CH2:24][C:25]3[CH:26]=[C:27]([CH:32]=[CH:33][CH:34]=3)[C:28]([O:30]C)=[O:29])[CH3:23])=[C:18]([CH3:35])[CH:17]=2)=[C:12]([CH:36]([CH3:38])[CH3:37])[O:11][N:10]=1.[OH-].[Li+]>O1CCCC1>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[C:9]1[C:13]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]([CH2:24][C:25]3[CH:26]=[C:27]([CH:32]=[CH:33][CH:34]=3)[C:28]([OH:30])=[O:29])[CH3:23])=[C:18]([CH3:35])[CH:17]=2)=[C:12]([CH:36]([CH3:38])[CH3:37])[O:11][N:10]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69207637HCID 69207637, compound

Product 1

HCID 10256736HCID 10256736, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 3-{[(4-{[3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl]methoxy}-2-methylphenyl)(methyl)amino]methyl}benzoate (0.42 g, 0.76 mmol) in tetrahydrofuran (4 mL) was stirred vigorously with aqueous lithium hydroxide (2.3 ml, 0.4 M) at ambient temperature for 24 hours. The reaction was concentrated and the aqueous residue was partitioned with ethyl acetate and aqueous sodium hydrogensulfate. The organic layer was washed with brine (50 mL) and was dried over anhydrous magnesium sulfate, filtered, and condensed to a residue which was chromatographed on silica gel eluting with 10% methanol/dichloromethane. Yield=0.12 g. (30%) of 3-{[(4-{[3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl]methoxy}-2-methylphenyl)(methyl)amino]methyl}benzoic acid. 1H NMR (CDCl3, 400 MHz) δ 8.02 (s, 1H), 7.91 (d, 1H), 7.55 (d, 1H), 7.38 (m 3H), 7.31 (m, 1H), 6.95 (d, 1H), 6.33 (m, 1H), 6.57 (dd, 1H), 4.67 (s, 2H), 3.97 (s, 2H), 3.91 (s, 3H), 3.31 (m, 1H), 2.49 (s, 3H), 2.33 (s, 3H), 1.40 (d, 6H); MS (ESP+) m/e 539 (MH+).

Workup

  1. concentrationThe reaction was concentrated
  2. customthe aqueous residue was partitioned with ethyl acetate and aqueous sodium hydrogensulfate
  3. washThe organic layer was washed with brine (50 mL)
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customcondensed to a residue which
  7. customwas chromatographed on silica gel eluting with 10% methanol/dichloromethane

Sources & evidence

ORD record
ord-23a84b3a3c714f7e9d7959fea23e1f1f
Source dataset
uspto-grants-2008_01
Patent number
US07319109B2

Reaction notes

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