Hydrogen Peroxide → (2S,3R)-5-(4'-fluorobiphenyl-4-yl)-3-hydroxy-2-[(4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl]pentanoic acid

HRID 2410466Notes

Reaction equation

HRID 2410466 reaction equation
C([C@H]1CSC(=O)N1[C:14]([C@@H:16]([C@@H:29]([OH:45])[CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]2[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=2)=[CH:34][CH:33]=1)[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:15])C1C=CC=CC=1.[OH:46]O.O.[OH-].[Li+]>O1CCCC1.O.O>[F:44][C:41]1[CH:40]=[CH:39][C:38]([C:35]2[CH:36]=[CH:37][C:32]([CH2:31][CH2:30][C@@H:29]([OH:45])[C@H:16]([CH2:17][N:18]3[C:23](=[O:24])[C:22]4[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=4[N:20]=[N:19]3)[C:14]([OH:15])=[O:46])=[CH:33][CH:34]=2)=[CH:43][CH:42]=1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 168937Lithium hydroxide, monohydrateHCID 671830643-[(2R,3S)-2-{[(4S)-4-benzyl-2-oxo-1,3-thiazolidin-3-yl]carbonyl}-5-(4'-fluorobiphenyl-4-yl)-3-hydroxypentyl]-1,2,3-benzotriazin-4(3H)-one

Product 1

HCID 67183397(2S,3R)-5-(4'-fluorobiphenyl-4-yl)-3-hydroxy-2-[(4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl]pentanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of the compound obtained from step f above (0.18 g) in tetrahydrofuran:water (3:1, 10 mL), aqueous hydrogen peroxide solution (30%, 0.15 mL) was added at 0° C., followed by the addition of lithium hydroxide monohydrate (17.6 mg) in water (2 mL). The reaction mixture was stirred at 0° C. until the completion of the hydrolysis. The reaction mixture was concentrated and the residue was extracted with ethyl acetate. The aqueous layer was acidified with sodium hydrogen sulphate and extracted with ethyl acetate. The combined layers were washed with water and brine, and dried over anhydrous sodium sulphate. The solvents were evaporated under reduced pressure and the crude residue was purified by silica gel flash column chromatography using 10% methanol in dichloromethane as eluant to afford the title compound (0.075 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionthe residue was extracted with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. washThe combined layers were washed with water and brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. customThe solvents were evaporated under reduced pressure
  7. customthe crude residue was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-73791640f5e94a03976dbf6fdaf22918
Source dataset
uspto-grants-2014_08
Patent number
US08816073B2

Reaction notes

Loading…