Lithium Hydroxide → HCID 69967796, compound

HRID 2289127Notes

Reaction equation

HRID 2289127 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:29][C:30]([O:32]C)=[O:31])[CH:5]=[CH:6][C:7]=1[NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]2[C:17]([C:25]([F:28])([F:27])[F:26])=[N:18][O:19][C:20]=2[C:21]=1[CH2:22][CH2:23][CH3:24].[OH-].[Li+]>CO.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:29][C:30]([OH:32])=[O:31])[CH:5]=[CH:6][C:7]=1[NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]2[C:17]([C:25]([F:28])([F:26])[F:27])=[N:18][O:19][C:20]=2[C:21]=1[CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 70253217HCID 70253217, compound

Product 1

HCID 69967796HCID 69967796, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of Methyl 3-chloro-4-(3-(3-trifluoromethyl-7-propyl-6-benz-[4,5]-isoxazoloxy)propylamino)-phenylacetate (Step C, 0.113 grams) in methanol (1.5 mL) was treated with a solution of lithium hydroxide in water (1.01 M; 0.362 mL). The reaction was refluxed 1 hour. The reaction mixture was partitioned between isopropyl acetate and 0.1N HCl. The organic was dried over magnesium sulfate, filtered and concentrated to a solid. The solid was suspended in methylene chloride/cyclohexane (1:1; 2 mL). The mixture was refluxed briefly and cooled to 0° C. The title compound was isolated by filtration.

Workup

  1. temperatureThe reaction was refluxed 1 hour
  2. customThe reaction mixture was partitioned between isopropyl acetate and 0.1N HCl
  3. dry with materialThe organic was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to a solid
  6. temperatureThe mixture was refluxed briefly

Sources & evidence

ORD record
ord-23e1d65f977d49a88db8c111ee0edd20
Source dataset
uspto-grants-2000_07
Patent number
US06090836

Reaction notes

Loading…