Sodium Hydroxide → HCID 178524367, compound

HRID 1689795Notes

Reaction equation

HRID 1689795 reaction equation
C[O:2][C:3](=[O:34])[C:4]1[CH:9]=[CH:8][C:7]([C@H:10]2[CH2:15][CH2:14][C@H:13]([O:16][CH2:17][C:18]3[C:19]([C:26]4[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:27]=4[Cl:33])=[N:20][O:21][C:22]=3[CH:23]3[CH2:25][CH2:24]3)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1.[OH-].[Na+]>O1CCCC1.CO>[CH:23]1([C:22]2[O:21][N:20]=[C:19]([C:26]3[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:27]=3[Cl:33])[C:18]=2[CH2:17][O:16][C@H:13]2[CH2:14][CH2:15][C@H:10]([C:7]3[CH:6]=[CH:5][C:4]([C:3]([OH:34])=[O:2])=[CH:9][CH:8]=3)[CH2:11][CH2:12]2)[CH2:25][CH2:24]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178497882HCID 178497882, compound

Product 1

HCID 178524367HCID 178524367, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
52 °C

Procedure

Trans-4-{4-[5-cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-ylmethoxy]-cyclohexyl}-benzoic acid methyl ester (823.31 μmoles; 412.00 mg) is dissolved in tetrahydrofuran (8 mL) and methanol (10 mL). 2N aqueous NaOH (2.5 mL, 5 mmol) is added and the mixture is heated to 52° C. for 2 h. The reaction mixture is cooled and concentrated under reduced pressure. The residue is diluted with water (10 mL) and acidified with 5N HCl (1 mL). The solid is collected by filtration, washed with water, and dried in vacuo to give the title compound (313 mg, 78%) as a white solid. MS m/z 487.8 (M+1).

Workup

  1. temperatureThe reaction mixture is cooled
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue is diluted with water (10 mL)
  4. filtrationThe solid is collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-2f5ed77cead7444db593ee9d6c2a40d2
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

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