Sodium Hydroxide → 3-[2-Carboxy-2-(4-methoxy-6-methyl-2-pyrimidinyloxy)-1,1-diphenylethoxy]-2,2-dimethylpropionic Acid

HRID 397333Notes

Reaction equation

HRID 397333 reaction equation
C[O:2][C:3]([CH:5]([O:28][C:29]1[N:34]=[C:33]([O:35][CH3:36])[CH:32]=[C:31]([CH3:37])[N:30]=1)[C:6]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[O:7][CH2:8][C:9]([CH3:15])([CH3:14])[C:10]([O:12]C)=[O:11])=[O:4].[OH-].[Na+]>O1CCOCC1.O>[C:3]([CH:5]([O:28][C:29]1[N:34]=[C:33]([O:35][CH3:36])[CH:32]=[C:31]([CH3:37])[N:30]=1)[C:6]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[O:7][CH2:8][C:9]([CH3:15])([CH3:14])[C:10]([OH:12])=[O:11])([OH:4])=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 15379669Methyl 3-[2-Methoxycarbonyl-2-(4-methoxy-6-methyl-2-pyrimidinyloxy)-1,1-diphenylethoxy]-2,2-dimethylpropionate

Product 1

HCID 230001543-[2-Carboxy-2-(4-methoxy-6-methyl-2-pyrimidinyloxy)-1,1-diphenylethoxy]-2,2-dimethylpropionic AcidYield 42.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

10.1 g (20 mmol) of methyl 3-[2-methoxycarbonyl-2-(4-methoxy-6-methyl-2-pyrimidinyloxy)-1,1-diphenylethoxy]-2,2-di-methylpropionate were dissolved in 50 ml of dioxane and 50 ml of 2N NaOH solution and stirred at 80° C. for 4 h. The solution was diluted with 300 ml of H2O and extracted with 100 ml of ethyl acetate. The aqueous phase was neutralized with 1N HCl and extracted with ethyl acetate, and the organic phase was dried over MgSO4, filtered and concentrated. The oily residue was crystallized from diethyl ether/hexane to result in 4.1 g (42%) of colorless crystals.

Workup

  1. extractionextracted with 100 ml of ethyl acetate
  2. extractionextracted with ethyl acetate
  3. dry with materialthe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe oily residue was crystallized from diethyl ether/hexane

Sources & evidence

ORD record
ord-5bfa9418378d41ba9b2c0e7b8abaff7b
Source dataset
uspto-grants-2003_08
Patent number
US06610691B1

Reaction notes

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