Sodium Thiosulfate → HCID 86638498, compound

HRID 216342Notes

Reaction equation

HRID 216342 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH2:23]([O:25][P:26]([C:31]([F:50])([F:49])[CH:32]([C:34]1[CH:39]=[CH:38][C:37]([C:40]2[CH:45]=[CH:44][C:43]([F:46])=[CH:42][N:41]=2)=[C:36]([F:47])[C:35]=1[F:48])[OH:33])(=[O:30])[O:27][CH2:28][CH3:29])[CH3:24].C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[F:48][C:35]1[C:36]([F:47])=[C:37]([C:40]2[CH:45]=[CH:44][C:43]([F:46])=[CH:42][N:41]=2)[CH:38]=[CH:39][C:34]=1[C:32](=[O:33])[C:31]([P:26](=[O:30])([O:27][CH2:28][CH3:29])[O:25][CH2:23][CH3:24])([F:49])[F:50]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 86638494Diethyl{2-[2,3-difluoro-4-(5-fluoropyridin-2-yl)phenyl]-1,1-difluoro-2-hydroxyethyl}phosphonate

Product 1

HCID 86638498HCID 86638498, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin reagent (1.75 g, 4.1 mmol) was added to a solution of diethyl{2-[2,3-difluoro-4-(5-fluoropyridin-2-yl)phenyl]-1,1-difluoro-2-hydroxyethyl}phosphonate (876 mg, 2.1 mmol) in methylene chloride (30 mL) at room temp—solution darkens to deep red over 1 hr. After stirring at rt for 1 hr, a solution of saturated aqueous sodium bicarbonate and saturated aqueous sodium thiosulfate (1:1) (ca. 20 mL) was added and the solution stirred until clear. The reaction mixture was extracted with dichloromethane, dried (sodium sulfate) and concentrated to afford diethyl {2-[2,3-difluoro-4-(5-fluoropyridin-2-yl)phenyl]-1,1-difluoro-2-oxoethyl}phosphonate as an off white solid which was used without further purification.

Workup

  1. stirringthe solution stirred until clear
  2. extractionThe reaction mixture was extracted with dichloromethane
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-72e8b7a7e0f84e2c9dfe9f3621849c8b
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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