Triacetoxyperiodinane → HCID 70301180, compound

HRID 850653Notes

Reaction equation

HRID 850653 reaction equation
[C:1]([O:5][C:6]([CH:8]([CH:14]([OH:56])[C:15](=[O:55])[N:16]([CH:28]([CH3:54])[CH:29]([C:45]1[CH:50]=[CH:49][C:48]([N+:51]([O-:53])=[O:52])=[CH:47][CH:46]=1)[CH2:30][C:31]1[O:32][C:33]([C:36](=[O:44])[NH:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[CH:34][CH:35]=1)[CH2:17][C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=1)[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([C:8](=[C:14]([OH:56])[C:15](=[O:55])[N:16]([CH:28]([CH3:54])[CH:29]([C:45]1[CH:50]=[CH:49][C:48]([N+:51]([O-:53])=[O:52])=[CH:47][CH:46]=1)[CH2:30][C:31]1[O:32][C:33]([C:36](=[O:44])[NH:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)=[CH:34][CH:35]=1)[CH2:17][C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=1)[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 19364509HCID 19364509, compound

Product 1

HCID 70301180HCID 70301180, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

40 mg of methyl 3-tert-butoxycarbonyl-4-hydroxy-4-[N-[(1RS,2RS)-1-methyl-2-(4-nitrophenyl)-3-{5-(phenylcarbamoyl)-2-furyl}propyl]-N-(2-naphthylmethyl)carbamoyl]butanoate was dissolved in 5 ml of chloroform, and 68 mg of Dess-Martin reagent was added thereto, followed by stirring at room temperature for one hour. The reaction solution was poured into a mixed solution of a saturated sodium hydrogencarbonate aqueous solution and a saturated sodium thiosulfate aqueous solution and extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The drying agent was filtered off, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel thin layer chromatography (Kieselgel™60F254, Art™5744; hexane/ethyl acetate=3/2) to obtain 16 mg (yield: 40%) of the above-identified compound as a colorless oily substance.

Workup

  1. extractiona saturated sodium thiosulfate aqueous solution and extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe drying agent was filtered off
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel thin layer chromatography (Kieselgel™60F254, Art™5744; hexane/ethyl acetate=3/2)

Sources & evidence

ORD record
ord-17e712070e944edf917e5ce16f041006
Source dataset
uspto-grants-2000_01
Patent number
US06017956

Reaction notes

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