Chloroform → HCID 86675058, compound

HRID 1912107Notes

Reaction equation

HRID 1912107 reaction equation
[CH:1]1([C:4]2[N:8]([CH:9]3[CH2:12][CH:11]([CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:10]3)[N:7]=[N:6][C:5]=2[CH:17]([CH2:26][CH2:27][OH:28])[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:3][CH2:2]1.C(Cl)(Cl)Cl.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH:1]1([C:4]2[N:8]([CH:9]3[CH2:10][CH:11]([CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:12]3)[N:7]=[N:6][C:5]=2[CH:17]([CH2:26][CH:27]=[O:28])[CH2:18][C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 71127315HCID 71127315, compound

Product 1

HCID 86675058HCID 86675058, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 3-[5-cyclopropyl-1-(3-isobutylcyclobutyl)-1H-[1,2,3]triazol-4-yl]-5-hydroxyvalerate (106 mg) and chloroform (1 mL) were mixed. To the mixture was added Dess-Martin reagent (130 mg) at ice temperature. After stirring at RT for 1 hr, saturated aqueous sodium bicarbonate and ethyl acetate were added to the mixture at ice temperature. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate, water and brine, then dried over magnesium sulfate. The magnesium sulfate was filtered off and the filtrate was concentrated in vacuo to give the title compound (106 mg) as a crude product.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate, water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe magnesium sulfate was filtered off
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-53287ad365a74675a88c8b31dc642327
Source dataset
uspto-grants-2013_12
Patent number
US08604069B2

Reaction notes

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