Water → HCID 19045487, compound

HRID 1781388Notes

Reaction equation

HRID 1781388 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[CH:8][C:9]2[O:23][C:13]3([CH2:18][CH2:17][N:16]([CH2:19][CH2:20]SC)[CH2:15][CH2:14]3)[CH2:12][C:11](=[O:24])[C:10]=2[CH:25]=1)(=O)=[O:3].O[O:27][S:28]([O-:30])=O.[K+].[C:32]([O-])(O)=O.[Na+].[OH2:37]>CO>[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[CH:8][C:9]2[O:23][C:13]3([CH2:18][CH2:17][N:16]([CH2:19][CH2:20][S:28]([CH3:32])(=[O:30])=[O:27])[CH2:15][CH2:14]3)[CH2:12][C:11](=[O:24])[C:10]=2[CH:25]=1)(=[O:3])=[O:37]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 19045479HCID 19045479, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 19045487HCID 19045487, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 6-methanesulfonamido-3,4-dihydro-1'-(2-methylthioethyl)spiro[(2H)-1-benzopyran-2,4'-piperidine]-4-one (0.335 g, 0.871 mmol) in 15 mL of methanol was treated dropwise with a solution of Oxone® (0.803 g, 1.31 mmol) in 15 mL of water. The resulting mixture was stirred at 25° C. for 2 hours. The reaction mixture was then poured into 50 mL of saturated aqueous NaHCO3 and extracted with a total of 100 mL of ethyl acetate. The organic phase was dried (MgSO4), filtered, and concentrated in vacuo to a pale yellow oil which was shown to be a mixture by then layer analysis. The mixture was chromatographed on silica gel using 5% methanol in methylene chloride eluant. The pure oil was dissolved in 20 mL of absolute ethanol and was treated with excess 4.8N ethanolic HCl. The solid was collected, washed with diethyl ether, and dried for 4 hours at 100° C. under vacuum to give 0.176 g (44.6%) of product, mp 250°-251° C.

Workup

  1. extractionextracted with a total of 100 mL of ethyl acetate
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo to a pale yellow oil which
  5. customThe mixture was chromatographed on silica gel using 5% methanol in methylene chloride eluant
  6. dissolutionThe pure oil was dissolved in 20 mL of absolute ethanol
  7. additionwas treated with excess 4.8N ethanolic HCl
  8. customThe solid was collected
  9. washwashed with diethyl ether
  10. customdried for 4 hours at 100° C. under vacuum

Sources & evidence

ORD record
ord-21549f1abd034e7fa819e5d32eb716a4
Source dataset
uspto-grants-1997_05
Patent number
US05633247

Reaction notes

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