Triacetoxyperiodinane → HCID 69720245, compound

HRID 263674Notes

Reaction equation

HRID 263674 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1/[CH:10]=[CH:11]/[CH2:12][C@H:13]([C:45]1[CH:50]=[CH:49][C:48]2[O:51][CH2:52][O:53][C:47]=2[CH:46]=1)[C@H:14]([N:16]([CH2:34][C:35]1[CH:44]=[CH:43][C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:36]=1)[C:17]([C@@H:19]([OH:33])[C@@H:20]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:21][C:22]([O:24][CH3:25])=[O:23])=[O:18])[CH3:15].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1/[CH:10]=[CH:11]/[CH2:12][C@H:13]([C:45]1[CH:50]=[CH:49][C:48]2[O:51][CH2:52][O:53][C:47]=2[CH:46]=1)[C@H:14]([N:16]([CH2:34][C:35]1[CH:44]=[CH:43][C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:36]=1)[C:17]([C:19]([OH:33])=[C:20]([C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])[CH2:21][C:22]([O:24][CH3:25])=[O:23])=[O:18])[CH3:15]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 86751030HCID 86751030, compound

Product 1

HCID 69720245HCID 69720245, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

36 mg of methyl (3S,4S)-4-[N-{(1R,2R,4E)-5-(2-benzoxazolyl)-1-methyl-2-(3,4-methylenedioxyphenyl)-4-pentenyl}-N-(2-naphthylmethyl)carbamoyl]-3-tert-butoxycarbonyl-4-hydroxybutanoate was dissolved in 2 ml of chloroform, and 42 mg of a Dess-Martin reagent (periodenane) was added thereto, followed by stirring at room temperature for 1 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 then, 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 14.7 mg (yield: 41%) of the above-identified compound as 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-3c992e0e82b64c14b5ea3ada62bb194c
Source dataset
uspto-grants-1997_07
Patent number
US05643958

Reaction notes

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