Sodium Thiosulfate → HCID 59721726, compound

HRID 1671623Notes

Reaction equation

HRID 1671623 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Cl:23][C:24]1[CH:41]=[CH:40][C: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])=[CH:26][CH:25]=1.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[Cl:23][C:24]1[CH:41]=[CH:40][C: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])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 25209689HCID 25209689, compound

Product 1

HCID 59721726HCID 59721726, 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 4-chlorobenzyl(2-hydroxyethyl)carbamate (II-2) (0.29 g, 0.001 mol) in anhydrous CH2Cl2 (5 mL). Then the reaction mixture was stirred at room temperature for 21 h under N2 atmosphere. 1 M of Na2S2O3 (10 mL) was added to the reaction mixture, and after stirring 10 min, the reaction mixture was extracted with CH2Cl2 (10 mL×3). The combined organic layers were washed with 5% aqueous NaHCO3 (20 mL), and brine (20 mL). The organic layer was dried over Na2SO4, and evaporated in vacuo. The residue was then purified by column chromatography (silica gel, Hexanes:EtoAc=8:2) to afford colorless oil (IV-1, 0.20 g, 72%).

Workup

  1. stirringafter stirring 10 min
  2. extractionthe reaction mixture was extracted with CH2Cl2 (10 mL×3)
  3. washThe combined organic layers were washed with 5% aqueous NaHCO3 (20 mL), and brine (20 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customevaporated in vacuo
  6. customThe residue was then purified by column chromatography (silica gel, Hexanes:EtoAc=8:2)
  7. customto afford colorless oil (IV-1, 0.20 g, 72%)

Sources & evidence

ORD record
ord-ea08ef9a78604d21b7ee8fc4324a802a
Source dataset
uspto-grants-2011_08
Patent number
US07994326B2

Reaction notes

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