Hydrochloric Acid → HCID 68478089, compound

HRID 2265091Notes

Reaction equation

HRID 2265091 reaction equation
[CH3:1][Si:2]([CH3:34])([CH3:33])[C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([Si:29]([CH3:32])([CH3:31])[CH3:30])[CH:28]=1)[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12](/[C:15](/[CH3:24])=[CH:16]/[C:17]([O:19]CCCC)=[O:18])=[C:11]([CH3:25])[CH:10]=1)=[O:7].[OH-].[K+].Cl>O1CCCC1>[CH3:32][Si:29]([CH3:30])([CH3:31])[C:27]1[CH:26]=[C:5]([CH:4]=[C:3]([Si:2]([CH3:1])([CH3:33])[CH3:34])[CH:28]=1)[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12](/[C:15](/[CH3:24])=[CH:16]/[C:17]([OH:19])=[O:18])=[C:11]([CH3:25])[CH:10]=1)=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 86644276HCID 86644276, compound

Product 1

HCID 68478089HCID 68478089, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 5c (304 mg) was dissolved in tetrahydrofuran (12 ml) and a 4.4% potassium hydroxide solution (8 ml) was added to the obtained mixture. The mixture was stirred at room temperature for 12 hours, and was further stirred under heating at 50° C. for 3 hours. The reaction mixture was allowed to cool, and a 2N hydrochloric acid aqueous solution was added thereto. The mixture was separated with ethyl acetate and water. The organic layer was sequentially washed once with a saturated sodium bicarbonate aqueous solution and once with a saturated sodium chloride solution, and then dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was recrystallized with a mixed solvent of diethyl ether and n-hexane to obtain Compound 5 (164 mg, 61%).

Workup

  1. stirringwas further stirred
  2. temperatureunder heating at 50° C. for 3 hours
  3. temperatureto cool
  4. customThe mixture was separated with ethyl acetate and water
  5. washThe organic layer was sequentially washed once with a saturated sodium bicarbonate aqueous solution and once with a saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe obtained residue was recrystallized with a mixed solvent of diethyl ether and n-hexane

Sources & evidence

ORD record
ord-9cbe59833cf94dffbee2bd1f7e409320
Source dataset
uspto-grants-2010_12
Patent number
US07855300B2

Reaction notes

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