Sodium Thiosulfate → HCID 90407219, compound

HRID 1526517Notes

Reaction equation

HRID 1526517 reaction equation
[CH2:1]([C@:8]1([C:23]([NH:25][CH:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:27][OH:28])=[O:24])[O:12][C:11](=[O:13])[N:10]([C@@H:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:15])[C:9]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.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+]>ClCCl>[CH2:1]([C@:8]1([C:23]([NH:25][CH:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:27]=[O:28])=[O:24])[O:12][C:11](=[O:13])[N:10]([C@@H:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:15])[C:9]1=[O:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 90407404HCID 90407404, compound

Product 1

HCID 90407219HCID 90407219, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the product from Step A (250 mg, 0.545 mmol) in dichloromethane (5 mL) was added Dess-Martin periodinane (358 mg, 0.818 mmol) and the mixture was stirred for 30 min. A 1:1 mixture of saturated aqueous sodium bicarbonate and saturated aqueous sodium thiosulfate (20 mL) was added and the mixture was stirred rapidly for 15 min. The layers were separated and the aqueous phase extracted with dichloromethane (3×10 mL). The combined organic phases were washed with saturated aqueous brine (1×15 mL), dried with anhydrous sodium sulfate, filtered and the solvent removed in vacuo, to afford the crude colorless title compound as an amorphous solid. LC/MS 457.1 (M+1).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred rapidly for 15 min
  3. customThe layers were separated
  4. extractionthe aqueous phase extracted with dichloromethane (3×10 mL)
  5. washThe combined organic phases were washed with saturated aqueous brine (1×15 mL)
  6. dry with materialdried with anhydrous sodium sulfate
  7. filtrationfiltered
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-0d37da23f0ab49219cc195bc0a4ff2b7
Source dataset
uspto-grants-2015_07
Patent number
US09085568B2

Reaction notes

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