Sodium Thiosulfate → HCID 15660993, compound

HRID 35872Notes

Reaction equation

HRID 35872 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[C:5]([F:29])([F:28])[CH:6]([C@@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13](=[O:27])[CH2:14][CH2:15][C:16](=[O:26])[N:17]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:18])[OH:7])[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.CCOCC>[CH2:1]([O:3][C:4](=[O:30])[C:5]([F:28])([F:29])[C:6]([C@@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13](=[O:27])[CH2:14][CH2:15][C:16](=[O:26])[N:17]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:18])=[O:7])[CH3:2]

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 15660992HCID 15660992, compound

Product 1

HCID 15660993HCID 15660993, compoundYield 95.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of (3RS)-3-[(2S)-l-[3-(N-benzyl-N-methylcarbamoyl) propanoyl]pyrrolidin-2-yl]-3-hydroxy-2,2-difluoropropionic acid ethyl ester (250 mg) in methylene chloride (1.5 ml) was added dropwise to a suspension of Dess-Martin reagent (448 mg) in methylene chloride (6 ml). The mixture was stirred for 3 hrs. The reaction mixture was diluted with ether. A saturated aq. solution of sodium bicarbonate (30 ml) wherein sodium thiosulfate (2.26 g) was dissolved was added to the diluted solution. The mixture was stirred for 10 mins, and extracted with EtOAc. The extract was washed, dried and evaporated. The residue was purified by column chromatography on silica gel (hexane - EtoAc) to give the title compound (238 mg) having the following physical data:

Workup

  1. additionwas added to the diluted solution
  2. stirringThe mixture was stirred for 10 mins
  3. extractionextracted with EtOAc
  4. washThe extract was washed
  5. customdried
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica gel (hexane - EtoAc)

Sources & evidence

ORD record
ord-b6cb9c4afea24e07858649ab85e6f3f0
Source dataset
uspto-grants-1995_05
Patent number
US05411974

Reaction notes

Loading…