Sodium Thiosulfate → HCID 59909746, compound

HRID 1350279Notes

Reaction equation

HRID 1350279 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:19]([NH:21][CH:22]([C:26]([O:28][CH3:29])=[O:27])[CH:23]([OH:25])[CH3:24])=[O:20])[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])O.[Na+]>ClCCl>[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:19]([NH:21][CH:22]([C:26]([O:28][CH3:29])=[O:27])[C:23](=[O:25])[CH3:24])=[O:20])[CH2:11][C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 59909827HCID 59909827, compound

Product 1

HCID 59909746HCID 59909746, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl(3R)-6-cyclohexyl-3-({[2-hydroxy-1-(methoxycarbonyl)propyl]amino}carbonyl)hexanoate (Preparation 171) (6.48 g, 15.69 mmol) in dichloromethane (60 ml) was treated with Dess-Martin periodinane [1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one] (7.32 g, 17.26 mmol) and the resulting mixture was stirred at room temperature under a nitrogen atmosphere for 1 hour. A solution of sodium thiosulphate (6 g in 50 ml water) and a saturated aqueous sodium hydrogen carbonate solution (50 ml) were then added to the mixture which was stirred for a further 10 minutes. The layers were separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were sequentially washed with water and brine, dried over anhydrous magnesium sulphate, filtered and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a gradient system of pentane:ethyl acetate (100:0 to 90:10) to afford the title compound as a colourless oil (4.86 g)

Workup

  1. stirringwas stirred for a further 10 minutes
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with dichloromethane
  4. washThe combined organic layers were sequentially washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel eluting with a gradient system of pentane:ethyl acetate (100:0 to 90:10)

Sources & evidence

ORD record
ord-35e7e18bf2df4d369f4d24bfaa5decdb
Source dataset
uspto-grants-2007_05
Patent number
US07214694B2

Reaction notes

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