Sodium Thiosulfate → HCID 69720245, compound

HRID 2287491Notes

Reaction equation

HRID 2287491 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+].S([O-])([O-])(=O)=S.[Na+].[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

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 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 in 2 ml of chloroform was stirred with 42 mg of the Dess-Martin reagent (periodenane) at room temperature for 1 hour. The reaction solution was poured into a mixture of saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium thiosulfate and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the solvent was evaporated in vacuo. The residue was purified by silica gel thin layer chromatography [Kieselgel™ 60F254, Art™ 5744; hexane/ethyl acetate=3/2] to give 14.7 mg (yield 41%) of the title compound as a colorless oily substance.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe desiccant was filtered off
  5. customthe solvent was evaporated in vacuo
  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-7a74614eb1c64df19685c5b30de9bf5e
Source dataset
uspto-grants-2000_07
Patent number
US06083985

Reaction notes

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