Sodium Hydroxide → HCID 15682565, compound

HRID 1590003Notes

Reaction equation

HRID 1590003 reaction equation
[OH-].[Na+].[N:3]1([C:9]([C:11]2[O:15][N:14]=[C:13]([CH3:16])[C:12]=2[C:17]([O:19]C)=[O:18])=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1>O.CO>[N:3]1([C:9]([C:11]2[O:15][N:14]=[C:13]([CH3:16])[C:12]=2[C:17]([OH:19])=[O:18])=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 15682564HCID 15682564, compound

Product 1

HCID 15682565HCID 15682565, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Under a nitrogen blanket and at -15° to -10° C., 1.0 g (25.0 mmol) of sodium hydroxide in 20 ml of water was dripped over a period of 4 hours into a solution of 5.7 g (22.6 mmol) of methyl 5-piperidinocarbonyl-3-methylisoxazole-4-carboxylate in 20 ml of methanol, and the mixture was stirred for 12 hours at room temperature. The solution was evaporated down, the residue was taken up in 100 ml of water, the pH was adjusted to 8-9, and the mixture was extracted once with 100 ml of diethyl ether. The mixture was acidified to a pH of 2 with 6N HCl, and extracted four times, each time with 100 ml of dichloromethane. The combined organic phases dried over magnesium sulfate and the solvent was stripped off under reduced pressure. Yield: 91%; mp.: 128°-130° C.

Workup

  1. customThe solution was evaporated down
  2. extractionthe mixture was extracted once with 100 ml of diethyl ether
  3. extractionextracted four times
  4. dry with materialThe combined organic phases dried over magnesium sulfate

Sources & evidence

ORD record
ord-485394c20e49444fadc758fa15534cd1
Source dataset
uspto-grants-1993_04
Patent number
US05201932

Reaction notes

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