Isopropanol → HCID 57025855, compound

HRID 728884Notes

Reaction equation

HRID 728884 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][C@H:8]([CH:11]=[C:12]([CH3:20])[CH2:13][P:14]([O:18][CH3:19])([O:16][CH3:17])=[O:15])[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].C([OH:25])(C)C.C(OCC)(=O)C>CC(C)=O.[O-2].[O-2].[O-2].[Cr+6].S(=O)(=O)(O)O>[C:1]([O:5][C:6]([NH:7][C@H:8]([CH:11]=[C:12]([CH3:20])[CH2:13][P:14]([O:16][CH3:17])([O:18][CH3:19])=[O:15])[C:9]([OH:25])=[O:10])=[O:21])([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 3

HCID 3776IsopropanolHCID 8857Ethyl AcetateHCID 57187635HCID 57187635, compound

Product 1

HCID 57025855HCID 57025855, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 1118Sulfuric AcidSolventHCID 10219390chromium (VI) trioxideSolvent

Procedure

To a solution of 0.323 g of 8 in 10 ml of acetone there is added 0.77 ml ofa solution that is 3.25 molar in chromium trioxide and 5.29 molar in sulphuric acid. The mixture is stirred at room temperature for 40 minutes and then there are added 2 ml of isopropanol followed by 50 ml of ethyl acetate. 0.1 g of activated carbon is then added to the mixture. After 10 minutes, the mixture is filtered and washed with 50 ml of ethyl acetate. The filtrate is extracted three times with 50 ml of 10% sodium hydrogen carbonate solution each time. The aqueous phase is extracted twice with 40ml of ethyl acetate each time, acidified to pH 1 using 2N hydrochloric acid, and then extracted three times with 70 ml of ethyl acetate each time. The organic extracts are washed with saturated sodium chloride solution, dried over magnesium sulphate and concentrated by evaporation. Chromatography on 8 g of silica gel using chloroform/methanol/acetic acid 18:1:1 as eluant yields 65 mg of 9. 1H-NMR (300 MHz, DMSO-d6): 1.37 (s, (CH3)3CO); 1.82 (d, J=2, CH3 --C(4)); 2.63 (d, J=22, 2H--C(5)); 3.61 (d, J=11, (CH3O)2PO); 4.62 (t, J=8, H--C(2)); 5.25 (m, H--C(3)); 7.18 (d, J=8, NH); 11.7-12.5 (CO2H).

Workup

  1. addition0.1 g of activated carbon is then added to the mixture
  2. waitAfter 10 minutes
  3. filtrationthe mixture is filtered
  4. washwashed with 50 ml of ethyl acetate
  5. extractionThe filtrate is extracted three times with 50 ml of 10% sodium hydrogen carbonate solution each time
  6. extractionThe aqueous phase is extracted twice with 40ml of ethyl acetate each time
  7. extractionextracted three times with 70 ml of ethyl acetate each time
  8. washThe organic extracts are washed with saturated sodium chloride solution
  9. dry with materialdried over magnesium sulphate
  10. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-4c1e10cfb37c460298c88e174ac87181
Source dataset
uspto-grants-1991_09
Patent number
US05051413

Reaction notes

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