Sodium Thiosulfate → HCID 53918998, compound

HRID 1004325Notes

Reaction equation

HRID 1004325 reaction equation
[CH2:1]([O:3][C:4]([C:6](=[C:15]([C:20](=[O:53])[N:21]([CH:33]([CH3:52])[CH:34]([CH2:50][OH:51])[CH2:35][C:36]1[O:37][C:38]([C:41](=[O:49])[NH:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[CH:39][CH:40]=1)[CH2:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=1)[O:16][CH2:17][O:18][CH3:19])[CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[O:5])[CH3:2].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>[CH2:1]([O:3][C:4]([C:6](=[C:15]([C:20](=[O:53])[N:21]([CH:33]([CH3:52])[CH:34]([CH:50]=[O:51])[CH2:35][C:36]1[O:37][C:38]([C:41](=[O:49])[NH:42][C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)=[CH:39][CH:40]=1)[CH2:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=1)[O:16][CH2:17][O:18][CH3:19])[CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 70129292HCID 70129292, compound

Product 1

HCID 53918998HCID 53918998, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

124 mg of tert-butyl 3-(ethoxycarbonyl)-4-[N-[(1RS,2RS)-2-(hydroxymethyl)-1-methyl-3-{5-(phenylcarbamoyl)-2-furyl}propyl]-N-(2-naphthylmethyl)carbamoyl]-4-(methoxymethyloxy)-3-butenoate was dissolved in 3 ml of chloroform and stirred with 288 mg of the Dess-Martin reagent (periodinane) at room temperature for 30 minutes. 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 distilled off under reduced pressure. The residue was purified by silica gel thin layer chromatography [Kieselgel™ 60F254, Art™5744; hexane/ethyl acetate=1/2] to give 65 mg (yield: 53%) of the title compound as a white solid.

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. 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=1/2]

Sources & evidence

ORD record
ord-ead2c866aed54cb7829e991272cfa2eb
Source dataset
uspto-grants-2000_04
Patent number
US06048894

Reaction notes

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