Hydrogen Peroxide → HCID 69937561, compound

HRID 1058303Notes

Reaction equation

HRID 1058303 reaction equation
C([C@@H]1COC(=O)N1[C:14](=[O:37])[C@H:15]([OH:36])[C@H:16]([C:23]1[CH:24]=[C:25]([CH:33]=[CH:34][CH:35]=1)[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1)C1C=CC=CC=1.[OH:38]O.[Li+].[OH-]>C1COCC1.O>[C:29]([O:28][C:26]([C:25]1[CH:24]=[C:23]([C@H:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[C@@H:15]([OH:36])[C:14]([OH:38])=[O:37])[CH:35]=[CH:34][CH:33]=1)=[O:27])([CH3:32])([CH3:30])[CH3:31]

Participants

6

Reactant 3

HCID 784Hydrogen Peroxide2×HCID 3939Lithium Hydroxide2×HCID 69939367HCID 69939367, compound

Product 1

HCID 69937561HCID 69937561, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) solution of tert-butyl 3-{(1R,2R)-3-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-2-hydroxy-3-oxo-1-pyridin-2-ylpropyl}benzoate from the previous step (0.068 g, 0.135 mmol) in THF (2 mL), was added 35% hydrogen peroxide (0.061 mL, 0.541 mmol) dropwise, then 1.0M LiOH (0.271 mL, 0.271 mmol) in H2O (0.4 mL). The reaction was stirred for 1.5 hours, at which time HPLC indicated incomplete reaction so additional 35% hydrogen peroxide (0.030 mL, 0.271 mmol) and 1.0M LiOH (0.135 mL, 0.135 mmol) in H2O (0.2 mL) were added and stirring continued for 1 hour. HPLC analysis showed complete consumption of starting material. The mixture was quenched with 10% aqueous Na2SO3 (1 mL) and saturated aqueous NaHCO3 (1 mL), diluted with H2O (20 mL), and washed with 2×20 mL CH2Cl2. The aqueous layer was acidified with 10% aqueous citric acid, extracted with 2×30 mL CH2Cl2, dried over MgSO4, filtered, and the solvent removed under reduced pressure to give (2R,3R)-3-[3-(tert-butoxycarbonyl)phenyl]-2-hydroxy-3-pyridin-2-ylpropanoic acid as a yellow oil (0.020 g, 43%). TPLC RT=1.44 min, method B; M+H=344.

Workup

  1. additionwere added
  2. stirringstirring
  3. waitcontinued for 1 hour
  4. customconsumption of starting material
  5. customThe mixture was quenched with 10% aqueous Na2SO3 (1 mL) and saturated aqueous NaHCO3 (1 mL)
  6. additiondiluted with H2O (20 mL)
  7. washwashed with 2×20 mL CH2Cl2
  8. extractionextracted with 2×30 mL CH2Cl2
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-586f58f170be4b00b4b01c78563fbfb6
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

Loading…