Hydrochloric Acid → HCID 66670687, compound

HRID 1005936Notes

Reaction equation

HRID 1005936 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)O)[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][CH: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)[N:12]=1

Participants

6

Reactant 3

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

Product 1

HCID 66670687HCID 66670687, compoundYield 64.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The resulting propionic acid derivative (25 mg, 0.053 mmol) was dissolved in a mixture of ethanol (2 mL) and water (1 mL). To the solution was then added lithium hydroxide monohydrate (6 mg). The mixture was stirred for 20 hours at room temperature, and after cooling with ice, cooled with ice, neutralized by addition of diluted hydrochloric acid, and then 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 distilled off under reduced pressure, to give 15 mg of the desired compound as colorless oil residue (yield 63%).

Workup

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

Sources & evidence

ORD record
ord-17afaf9cc4514b0ca05311d2144895cf
Source dataset
uspto-grants-2004_09
Patent number
US06787552B2

Reaction notes

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