Hydrochloric Acid → HCID 58022567, compound

HRID 2389307Notes

Reaction equation

HRID 2389307 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:19][CH2:20][CH2:21][C:22]([CH3:33])([C:28]([O:30]CC)=[O:29])[C:23]([O:25][CH2:26][CH3:27])=[O:24].[OH-].[K+].O.Cl>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:19][CH2:20][CH2:21][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])([CH3:33])[C:28]([OH:30])=[O:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 58022551HCID 58022551, compound

Product 1

HCID 58022567HCID 58022567, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the compound of Example 38 (16.8 g) in ethanol (167 mL) was added potassium hydroxide (2.40 g), and the resultant solution was stirred at 50° C. for 24 hours. To the reaction solution was added water, neutralized with 2 mol/L aqueous hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water and saturatedbrine in that order, and then dried over anhydrous sodium sulfate. The solvent was evaporated, and the resultant residue was purified by silica gel column chromatography (hexane ethyl acetate=1:1) to obtain the target product (11.2 g) as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturatedbrine in that order
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customthe resultant residue was purified by silica gel column chromatography (hexane ethyl acetate=1:1)

Sources & evidence

ORD record
ord-339a424e664a4e28869813eeb7e2a2b1
Source dataset
uspto-grants-2012_09
Patent number
US08273748B2

Reaction notes

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