Monobasic potassium phosphate → methyl N-(4-bromo-5-methylisoxazol-3-yl)leucinate

HRID 1744106Notes

Reaction equation

HRID 1744106 reaction equation
[Br:1][C:2]1[C:3]([N:8](C(OCC(Cl)(Cl)Cl)=O)[C@H:9]([C:14]([O:16][CH3:17])=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=[N:4][O:5][C:6]=1[CH3:7].OP([O-])(O)=O.[K+]>[Zn].C1COCC1>[Br:1][C:2]1[C:3]([NH:8][C@H:9]([C:14]([O:16][CH3:17])=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=[N:4][O:5][C:6]=1[CH3:7]

Participants

5

Reactant 2

HCID 516951Monobasic potassium phosphateHCID 69152129methyl N-(4-bromo-5-methylisoxazol-3-yl)-N-[(2,2,2-trichloroethoxy)carbonyl]leucinate

Product 1

HCID 69152086methyl N-(4-bromo-5-methylisoxazol-3-yl)leucinate

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a dry THF solution (20 mL) of methyl N-(4-bromo-5-methylisoxazol-3-yl)-N-[(2,2,2-trichloroethoxy)carbonyl]leucinate (1.19 g, 2.47 mmol) and activated zinc (10.1 g, 154 mmol) was added ca. 10 mL of 1 M KH2PO4 (10 mmol) at 0° C. The mixture was stirred for 1.5 hours, filtered through celite, washed with 150 mL ethyl acetate, and concentrated to a small volume. The mixture was then partitioned between ethyl acetate and saturated aqueous sodium bicarbonate, washed with brine, dried over sodium sulphate and concentrated in vacuo. The crude product was purified by flash chromatography (20% ethyl acetate/hexane) to afford methyl N-(4-bromo-5-methylisoxazol-3-yl)leucinate.

Workup

  1. filtrationfiltered through celite
  2. washwashed with 150 mL ethyl acetate
  3. concentrationconcentrated to a small volume
  4. customThe mixture was then partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  5. washwashed with brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0b8e3aed12184076909fe9851eebd254
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

Loading…