Trifluoroacetic acid → 3-(2-Methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-yl)propionic acid

HRID 856173Notes

Reaction equation

HRID 856173 reaction equation
FC(F)(F)C(O)=O.[CH3:8][C:9]1([CH2:20][CH2:21][C:22]([O:24]C(C)(C)C)=[O:23])[O:13][C:12]2=[N:14][C:15]([N+:17]([O-:19])=[O:18])=[CH:16][N:11]2[CH2:10]1>C(Cl)Cl>[CH3:8][C:9]1([CH2:20][CH2:21][C:22]([OH:24])=[O:23])[O:13][C:12]2=[N:14][C:15]([N+:17]([O-:19])=[O:18])=[CH:16][N:11]2[CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23081265Tert-butyl 3-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-yl)propionate

Product 1

HCID 230811063-(2-Methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-yl)propionic acidYield 51.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2 ml) was added to a solution of tert-butyl 3-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-yl) propionate prepared in Example 44 (0.72 g, 2.42 mmol) in methylene chloride (14 ml) followed by stirring at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure. The residue was crystallized from ethanol-methylene chloride to afford 3-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-yl)propionic acid (0.30 g, 51%) as a light yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue was crystallized from ethanol-methylene chloride

Sources & evidence

ORD record
ord-48138d9fa9c8436c9c39e22bf58f453e
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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