Hydrochloric Acid → HCID 23369810, compound

HRID 1900799Notes

Reaction equation

HRID 1900799 reaction equation
C([O:4][C:5]1[C:14]([CH:15]([CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH:16]2[O:18][CH2:17]2)=[CH:13][C:12]([CH3:28])=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9](=[O:29])[NH:10]2)(=O)C.Cl>O1CCCC1CO.[OH-].[Na+]>[Si:21]([O:20][CH2:19][CH:15]1[C:14]2[C:5](=[C:6]3[C:11](=[C:12]([CH3:28])[CH:13]=2)[NH:10][C:9](=[O:29])[CH:8]=[CH:7]3)[O:4][CH:16]1[CH2:17][OH:18])([C:24]([CH3:25])([CH3:27])[CH3:26])([CH3:23])[CH3:22]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 23369571HCID 23369571, compound

Product 1

HCID 23369810HCID 23369810, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 7360Tetrahydrofurfuryl alcoholSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

5-Acetoxy-6-[1-(tert-butyldimethylsilyloxy)methyl-2,3-epoxypropyl]-8-methylcarbostyril (6.10 g, 14.6 mmol) was dissolved in a solvent mixture (150 ml) of tetrahydrofuran methanol (1:1), to which aqueous 1N-NaOH solution (25 ml) was added. The mixture was stirred at 50° C. for 30 minutes. Concentrated HCl was added to adjust the pH to about 5. Extraction was carried out using chloroform--water. The organic phase was dried over sodium sulfate and condensed under reduced pressure. The resultant residue was recrystallized from chloroform--ether--n-hexane. As a result, 5.10 g the title compound (mixture of diasteromers, 3.1) was obtained as colorless powdery crystals (93.0%).

Workup

  1. additionwas added
  2. extractionExtraction
  3. dry with materialThe organic phase was dried over sodium sulfate and condensed under reduced pressure
  4. customThe resultant residue was recrystallized from chloroform

Sources & evidence

ORD record
ord-8d94b8ee307444139fd9694e85e3c24c
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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