Hydrochloric Acid → HCID 59837328, compound

HRID 1455787Notes

Reaction equation

HRID 1455787 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][C:25]([C:32]([O:34]CC)=[O:33])([CH3:31])[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:18]([Cl:37])[CH:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].Cl>C(O)C.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])([CH3:31])[C:32]([OH:34])=[O:33])=[C:18]([Cl:37])[CH:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 23078207HCID 23078207, compound

Product 1

HCID 59837328HCID 59837328, compoundYield 91.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

The compound of Example 152 (2.74 g) was dissolved in ethanol (10 mL). To this solution, potassium hydroxide (330 mg) was added and the mixture was stirred at 50° C. overnight. Subsequently, the reaction mixture was diluted with water. 2 mol/L hydrochloric acid was then added and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous solution of sodium chloride and the organic phase was dried over anhydrous magnesium sulfate and was concentrated. The residue was purified on a silica gel column chromatography (hexane:ethyl acetate=10:1 shifted to 2:1) to give the desired product as a yellow oil (2.38 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialthe organic phase was dried over anhydrous magnesium sulfate
  4. concentrationwas concentrated
  5. customThe residue was purified on a silica gel column chromatography (hexane:ethyl acetate=10:1 shifted to 2:1)

Sources & evidence

ORD record
ord-74e0aaf7079b47979a9815a19dd90ac5
Source dataset
uspto-grants-2009_01
Patent number
US07482491B2

Reaction notes

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