Water → HCID 66941869, compound

HRID 348729Notes

Reaction equation

HRID 348729 reaction equation
CO[C:3](=O)[CH:4]=[CH:5][C:6]1[S:10][C:9]2[CH:11]=[CH:12][C:13]([CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:14][C:8]=2[CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)O[C:36](=O)[C:35]2[CH:34]=CC=CC1=2)=O.O>ClCCl>[C:20]([O:19][C:17](=[O:18])[NH:16][CH2:15][C:13]1[CH:12]=[CH:11][C:9]2[S:10][C:6]([CH2:5][CH2:4][CH2:3][N:16]([CH2:34][CH2:35][CH3:36])[CH2:15][CH2:13][CH3:12])=[CH:7][C:8]=2[CH:14]=1)([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 962WaterHCID 159087TriacetoxyperiodinaneHCID 66941921HCID 66941921, compound

Product 1

HCID 66941869HCID 66941869, compoundYield 116.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound (356.0 mg) obtained in Example 120-4 was dissolved in anhydrous dichloromethane (10 ml) and added with Dess-Martin periodinane (manufactured by Aldrich Corporation) (563.7 mg), followed by stirring at room temperature for 40 minutes. Then, the solution was added with water and extracted with chloroform. The organic layer was washed with saturated saline solution and dried with anhydrous sodium sulfate. The solvent was distilled off and the residue was then purified through silica gel column chromatography (hexane/ethyl acetate). The purified product was dissolved in methanol (10 ml) and then added with di-n-propylamine (0.19 ml), trimethyl orthoformate (0.15 ml), and sodium cyanoborohydride (87.6 mg), followed by stirring at room temperature for 30 hours. The solution was added with water and then extracted with chloroform. The organic layer was washed with saturated saline solution and then dried with anhydrous sodium sulfate. Subsequently, the solvent was distilled off and the residue was purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the subject compound (241.9 mg) as a pale-yellow solid.

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with saturated saline solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue was then purified through silica gel column chromatography (hexane/ethyl acetate)
  6. dissolutionThe purified product was dissolved in methanol (10 ml)
  7. additionadded with di-n-propylamine (0.19 ml), trimethyl orthoformate (0.15 ml), and sodium cyanoborohydride (87.6 mg)
  8. stirringby stirring at room temperature for 30 hours
  9. additionThe solution was added with water
  10. extractionextracted with chloroform
  11. washThe organic layer was washed with saturated saline solution
  12. dry with materialdried with anhydrous sodium sulfate
  13. distillationSubsequently, the solvent was distilled off
  14. customthe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2779eb643a5d471e8d3f25970df27eb9
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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