Bromine → HCID 69152663, compound

HRID 1744157Notes

Reaction equation

HRID 1744157 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([N:7]([C:17]([O:19][CH2:20][C:21]([Cl:24])([Cl:23])[Cl:22])=[O:18])[C@H:8]([C:13]([O:15][CH3:16])=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11])[S:4][N:3]=1.[Br:25]Br>C(Cl)Cl.CC(O)=O>[Br:25][C:6]1[C:2]([CH3:1])=[N:3][S:4][C:5]=1[N:7]([C:17]([O:19][CH2:20][C:21]([Cl:23])([Cl:24])[Cl:22])=[O:18])[C@H:8]([C:13]([O:15][CH3:16])=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11]

Participants

5

Reactant 2

HCID 24408Bromine2×HCID 69152267HCID 69152267, compound

Product 1

HCID 69152663HCID 69152663, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl N-(3-methylisothiazol-5-yl)-N-[(2,2,2-trichloroethoxy)carbonyl]-L-leucinate (28.5 g, 68 mmol) in CH2Cl2 (250 mL) and AcOH (125 mL) was added bromine (8.5 mL, 165 mmol). The resulting red solution was stirred at room temperature for 4 h. A further aliquot of bromine (8.5 mL, 165 mmol) was added and the resulting solution was stirred at room temperature for 18 h. The reaction mixture was partitioned between EtOAc and water+aqueous NaHSO3 until the decolorization was complete. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromatography using EtOAc in hexane to afford methyl N-(4-bromo-3-methylisothiazol-5-yl)-N-[(2,2,2-trichloroethoxy)carbonyl]-L-leucinate as a yellow syrup.

Workup

  1. stirringthe resulting solution was stirred at room temperature for 18 h
  2. customThe reaction mixture was partitioned between EtOAc and water+aqueous NaHSO3 until the decolorization
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-5be788b4abe949ef8033109c604915a6
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

Loading…