Tetrahydrofuran → (2S,3R)-3-(formyloxy)-2-[2-(4-oxo-1,2,3-benzotriazin-3(4H)-yl)ethyl]-5-phenylpentanoic acid

HRID 84017Notes

Reaction equation

HRID 84017 reaction equation
[OH:1][C@@H:2]1[C@H:6]([OH:7])[O:5][C@H:4]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C@@H:3]1[CH2:16][CH2:17][N:18]1[C:23](=[O:24])[C:22]2[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=2[N:20]=[N:19]1.[O:29]1CCCC1.I([O-])(=O)(=O)=O.[Na+].[Mn]([O-])(=O)(=O)=O.[K+]>C(O)(C)(C)C>[CH:6]([O:5][C@H:4]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C@H:3]([CH2:16][CH2:17][N:18]1[C:23](=[O:24])[C:22]2[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=2[N:20]=[N:19]1)[C:2]([OH:1])=[O:29])=[O:7]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 516875Potassium PermanganateHCID 23667635Sodium periodateHCID 67182053HCID 67182053, compound

Product 1

HCID 86700971(2S,3R)-3-(formyloxy)-2-[2-(4-oxo-1,2,3-benzotriazin-3(4H)-yl)ethyl]-5-phenylpentanoic acid

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of the compound obtained from step b above (0.3 g) in tert-butanol:tetrahydrofuran (3 mL:3 mL) at 0° C., a solution of sodium metaperiodate (0.673 g in 3 mL of water) was added. The reaction mixture was stirred for 2 hours at the same temperature and potassium permanganate (0.025 g) was added at 0° C. After stirring the reaction mixture for an additional 6 hours at room temperature, the reaction mixture was evaporated and the residue was taken into water and extracted with ethyl acetate. The organic layer was washed with water and brine solution, and dried over anhydrous sodium sulphate. The solvent was evaporated under reduced pressure, to afford the title compound (0.3 g).

Workup

  1. additionwas added at 0° C
  2. customthe reaction mixture was evaporated
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and brine solution
  5. dry with materialdried over anhydrous sodium sulphate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-642d55d22fef44718018b81a798c95bc
Source dataset
uspto-grants-2014_09
Patent number
US08846910B2

Reaction notes

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