Hydrochloric Acid → HCID 10226335, compound

HRID 1005934Notes

Reaction equation

HRID 1005934 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]([CH:32]([CH3:34])[CH3:33])=[C:11]([CH2:13][CH2:14][CH:15]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]([CH3:31])([CH3:30])[C:25]([O:27]CC)=[O:26])=[CH:19][CH:18]=2)[OH:16])[N:12]=1.O.[OH-].[Li+].Cl>C(O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]([CH:32]([CH3:34])[CH3:33])=[C:11]([CH2:13][CH2:14][CH:15]([C:17]2[CH:18]=[CH:19][C:20]([O:23][C:24]([CH3:30])([CH3:31])[C:25]([OH:27])=[O:26])=[CH:21][CH:22]=2)[OH:16])[N:12]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 22675178HCID 22675178, compound

Product 1

HCID 10226335HCID 10226335, compoundYield 75.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The resulting propionic acid derivative (80 mg, 0.16 mmol) was dissolved in a mixture of ethanol (2 mL) and water (1 mL). To the solution was then added lithium hydroxide monohydrate (10 mg). The mixture was stirred for 20 hours at room temperature, cooled with ice, neutralized by addition of diluted hydrochloric acid, and subjected to extraction using ethyl acetate. The organic layer was collected, washed with water and brine, dried over anhydrous sodium sulfate, and filtered. The ethyl acetate was removed under reduced pressure, to give 55 mg of the desired compound as pale yellow oil residue (yield 73%).

Workup

  1. temperaturecooled with ice
  2. extractionsubjected to extraction
  3. customThe organic layer was collected
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe ethyl acetate was removed under reduced pressure

Sources & evidence

ORD record
ord-7a608d12e2e54346b719af547e1efd6b
Source dataset
uspto-grants-2004_09
Patent number
US06787552B2

Reaction notes

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