Sodium Thiosulfate → HCID 59721733, compound

HRID 1671626Notes

Reaction equation

HRID 1671626 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[F:23][C:24]1[CH:25]=[C:26]([CH:40]=[CH:41][CH:42]=1)[CH2:27][CH2:28][N:29]([CH2:37][CH2:38][OH:39])[C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[F:23][C:24]1[CH:25]=[C:26]([CH:40]=[CH:41][CH:42]=1)[CH2:27][CH2:28][N:29]([CH2:37][CH:38]=[O:39])[C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 25209181HCID 25209181, compound

Product 1

HCID 59721733HCID 59721733, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of Dess-Martin periodinane (0.51 g, 0.0012 mol) in anhydrous CH2Cl2 (10 mL) was added a solution of tert-butyl 3-fluorophenethyl(2-hydroxyethyl)carbamate (V-5b, 0.28 g, 0.001 mol) in anhydrous CH2Cl2 (5 mL) via a cannula, and the reaction mixture was stirred at room temperature for 18 h under a N2 atmosphere. Na2S2O3 (1 M, 10 mL) was then added to the reaction mixture. After being stirred for 10 min, the organic layer was separated. The aqueous layer was extracted with CH2Cl2 (15 mL×3). The combined organic layers were washed with 5% aqueous NaHCO3 (20 mL) and brine (20 mL), and dried over Na2SO4. The solvent was evaporated. The residue was then purified by column chromatography (silica gel, hexane:EtOAc=7.5:2.5) to afford a colorless oil (XII-8, 0.24 g, 83%).

Workup

  1. stirringAfter being stirred for 10 min
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted with CH2Cl2 (15 mL×3)
  4. washThe combined organic layers were washed with 5% aqueous NaHCO3 (20 mL) and brine (20 mL)
  5. dry with materialdried over Na2SO4
  6. customThe solvent was evaporated
  7. customThe residue was then purified by column chromatography (silica gel, hexane:EtOAc=7.5:2.5)
  8. customto afford a colorless oil (XII-8, 0.24 g, 83%)

Sources & evidence

ORD record
ord-9fd0d6c4c5d1467e925ac23118c75cb8
Source dataset
uspto-grants-2011_08
Patent number
US07994326B2

Reaction notes

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