Sodium Thiosulfate → HCID 89509949, compound

HRID 1526515Notes

Reaction equation

HRID 1526515 reaction equation
[CH2:1]([C@:8]1([C:23]([NH:25][CH2:26][CH:27]([C:29]2[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[C:31]([O:37][CH3:38])[CH:30]=2)[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][CH2:26][C:27]([C:29]2[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[C:31]([O:37][CH3:38])[CH:30]=2)=[O:28])=[O:24])[O:12][C:11](=[O:13])[N:10]([C@@H:14]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH3:15])[C:9]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 89509946HCID 89509946, compound

Product 1

HCID 89509949HCID 89509949, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the product from Step A (310 mg, 0.598 mmol) in dichloromethane (5 mL) was added Dess-Martin periodinane (392 mg, 0.897 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 517.1 (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-891bd972ba3848ee856b0c9bff8e761a
Source dataset
uspto-grants-2015_07
Patent number
US09085568B2

Reaction notes

Loading…