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

HRID 2410407Notes

Reaction equation

HRID 2410407 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][C:13]([C:16]3[CH:17]=[N:18][CH:19]=[N:20][CH:21]=3)=[CH:12][CH:11]=2)[C@@H:3]1[CH2:22][CH2:23][N:24]1[C:29](=[O:30])[C:28]2[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=2[N:26]=[N:25]1.[O:35]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:11]=[CH:12][C:13]([C:16]2[CH:21]=[N:20][CH:19]=[N:18][CH:17]=2)=[CH:14][CH:15]=1)[C@H:3]([CH2:22][CH2:23][N:24]1[C:29](=[O:30])[C:28]2[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=2[N:26]=[N:25]1)[C:2]([OH:1])=[O:35])=[O:7]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 516875Potassium PermanganateHCID 23667635Sodium periodateHCID 67184114HCID 67184114, compound

Product 1

HCID 86700967(2S,3R)-3-(formyloxy)-2-[2-(4-oxo-1,2,3-benzotriazin-3(4H)-yl)ethyl]-5-(4-pyrimidin-5-ylphenyl)pentanoic acid

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of the compound obtained from step m above (0.25 g) in tert-butanol: tetrahydrofuran (5 mL:5 mL) at 0° C., a solution of sodium metaperiodate (0.465 g in 5 mL of water) was added. The reaction mixture was stirred for 2 hours at the same temperature and potassium permanganate (0.017 g) was added at 0° C. After stirring the reaction mixture for an additional 6 hours at room temperature, the reaction mixture was evaporated on a rotary evaporator. 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 the reduced pressure to afford the title compound (0.25 g).

Workup

  1. additionwas added at 0° C
  2. customthe reaction mixture was evaporated on a rotary evaporator
  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 the reduced pressure

Sources & evidence

ORD record
ord-5a317c3ea1b44f0f9fe7a2560034f9a9
Source dataset
uspto-grants-2014_08
Patent number
US08816073B2

Reaction notes

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