Hydrochloric Acid → HCID 67461239, compound

HRID 1620002Notes

Reaction equation

HRID 1620002 reaction equation
[CH3:1][C:2]([CH:13]([C:16]([C:18]1[CH:32]=[CH:31][C:21]2[N:22]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:24][C:20]=2[CH:19]=1)=[O:17])[CH2:14][CH3:15])(C(OCC)=O)[C:3]([O:5]CC)=[O:4].O1CCOCC1.[OH-].[Li+].Cl>O>[CH3:1][CH:2]([CH:13]([C:16]([C:18]1[CH:32]=[CH:31][C:21]2[N:22]=[C:23]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[O:24][C:20]=2[CH:19]=1)=[O:17])[CH2:14][CH3:15])[C:3]([OH:5])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 312751,4-DioxaneHCID 67465123HCID 67465123, compound

Product 1

HCID 67461239HCID 67461239, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

850 mg (1.94 mmol) diethyl 2-methyl-2-[1-(2-phenyl-benzoxazole-6-carbonyl)-propyl]-malonate are mixed with 10 ml dioxane, then a solution of 300 mg (12.53 mmol) lithium hydroxide in 10 ml of water is added and the mixture is left overnight at RT with stirring. The next day the reaction mixture is acidified with 4N hydrochloric acid and extracted with DCM. The org. phase is dried on magnesium sulphate and concentrated by rotary evaporation i. V., the residue is stirred with 5 ml DMSO and 500 mg lithium chloride for 1.5 h at 150° C., the reaction mixture is purified by RP-HPLC.

Workup

  1. extractionextracted with DCM
  2. customphase is dried on magnesium sulphate
  3. concentrationconcentrated by rotary evaporation i
  4. stirring, the residue is stirred with 5 ml DMSO and 500 mg lithium chloride for 1.5 h at 150° C.
  5. customthe reaction mixture is purified by RP-HPLC

Sources & evidence

ORD record
ord-59ff6296163144bfac2b5a928f4fd0b1
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

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