HCID 69152663, compound → HCID 69151609, compound

HRID 1744158Notes

Reaction equation

HRID 1744158 reaction equation
[Br:1][C:2]1[C:3]([CH3:25])=[N:4][S:5][C:6]=1[N:7](C(OCC(Cl)(Cl)Cl)=O)[C@H:8]([C:13]([O:15][CH3:16])=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11]>CC(O)=O.[Zn]>[Br:1][C:2]1[C:3]([CH3:25])=[N:4][S:5][C:6]=1[NH:7][C@H:8]([C:13]([O:15][CH3:16])=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11]

Participants

4

Reactant 1

HCID 69152663HCID 69152663, compound

Product 1

HCID 69151609HCID 69151609, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of methyl N-(4-bromo-3-methylisothiazol-5-yl)-N-[(2,2,2-trichloroethoxy)carbonyl]-L-leucinate (24.2 g, 48.8 mmol) in TBF (350 mL) and AcOH (90 mL) was added zinc dust (18.0 g, 275 mmol). The resulting grey suspension was sonicated for 30 min and then stirred at room temperature for 2 h. The reaction mixture was filtered on a pad of celite and concentrated in vacuo. The resulting residue was partitioned between EtOAc and water. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromatography using Et2O in hexane to afford methyl N-(4-bromo-3-methylisothiazol-5-yl)-L-leucinate as a colorless oil which solidified upon standing for 1 h at room temperature under high vacuum to give a white solid.

Workup

  1. customThe resulting grey suspension was sonicated for 30 min
  2. filtrationThe reaction mixture was filtered on a pad of celite
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was partitioned between EtOAc and water
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-a00779912c8740e9a32a22a7903b99e0
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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