Sodium periodate → HCID 70052865, compound

HRID 356141Notes

Reaction equation

HRID 356141 reaction equation
[CH2:1]([S:7][CH2:8][C:9](=[O:34])[C@@H:10]([NH:15][C:16](=[O:33])[CH2:17][CH2:18][C@H:19]([CH3:32])[CH2:20][NH:21][C:22](=[O:31])[CH2:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:11][CH2:12][CH2:13][CH3:14])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.I([O-])(=O)(=O)=[O:36].[Na+]>CO.O>[CH2:1]([S:7]([CH2:8][C:9](=[O:34])[C@@H:10]([NH:15][C:16](=[O:33])[CH2:17][CH2:18][C@H:19]([CH3:32])[CH2:20][NH:21][C:22](=[O:31])[CH2:23][O:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH2:11][CH2:12][CH2:13][CH3:14])=[O:36])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 70049889HCID 70049889, compound

Product 1

HCID 70052865HCID 70052865, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

(s)-1-Furfurylthio-3-((s)-4-methyl-2-phenoxyacetylaminovalerylamino)-2-heptanone (176 mg) obtained in Example 3 was dissolved in methanol (10 ml) and water (10 ml). To the solution was added sodium metaperiodate (82 mg), and the mixture was reacted at room temperature for 48 hours. Then, methanol was removed in vacuo, saturated brine was added to the residue, and the resultant mixture was extracted with chloroform. The extract was washed with saturated brine, dried over sodium sulfate, and filtered. The filtrate was concentrated and chromatographed on a silica gel column, eluting with hexane:ethyl acetate (1:1) to give the titled product (66 mg).

Workup

  1. customthe mixture was reacted at room temperature for 48 hours
  2. customThen, methanol was removed in vacuo, saturated brine
  3. additionwas added to the residue
  4. extractionthe resultant mixture was extracted with chloroform
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated
  9. customchromatographed on a silica gel column
  10. washeluting with hexane:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-341ecded15524123aa8104a4ae920dde
Source dataset
uspto-grants-1998_11
Patent number
US05834508

Reaction notes

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