Lithium Hydroxide → 2-Ethyl-2-[1-methyl-2-oxo-2-(2-phenyl-benzoxazol-6-yl)-ethyl]-malonic acid

HRID 1619984Notes

Reaction equation

HRID 1619984 reaction equation
[CH2:1]([C:3]([CH:12]([CH3:30])[C:13](=[O:29])[C:14]1[CH:28]=[CH:27][C:17]2[N:18]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:20][C:16]=2[CH:15]=1)([C:8]([O:10]C)=[O:9])[C:4]([O:6]C)=[O:5])[CH3:2].[OH-].[Li+]>O1CCOCC1.O>[CH2:1]([C:3]([CH:12]([CH3:30])[C:13](=[O:29])[C:14]1[CH:28]=[CH:27][C:17]2[N:18]=[C:19]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[O:20][C:16]=2[CH:15]=1)([C:4]([OH:6])=[O:5])[C:8]([OH:10])=[O:9])[CH3:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67464947Dimethyl 2-ethyl-2-[1-methyl-2-oxo-2-(2-phenyl-benzoxazol-6-yl)-ethyl]-malonate

Product 1

HCID 674631882-Ethyl-2-[1-methyl-2-oxo-2-(2-phenyl-benzoxazol-6-yl)-ethyl]-malonic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

660 mg (1.13 mmol) dimethyl 2-ethyl-2-[1-methyl-2-oxo-2-(2-phenyl-benzoxazol-6-yl)-ethyl]-malonate are dissolved in 20 ml dioxane. Then 170 mg (7.10 mmol) lithium hydroxide, dissolved in 5 ml of water, are added and the mixture is stirred overnight at RT. The reaction mixture is extracted with DCM, the aqueous phase is acidified and extracted again with DCM. Then the org. phase is dried and the solv. is completely eliminated by rotary evaporation i.V. The residue is separated by RP-HPLC (basic).

Workup

  1. additionare added
  2. extractionThe reaction mixture is extracted with DCM
  3. extractionextracted again with DCM
  4. customphase is dried
  5. customThe residue is separated by RP-HPLC (basic)

Sources & evidence

ORD record
ord-12d5756b73e949b6bbaf9dbaaec275ee
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

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