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

HRID 856168Notes

Reaction equation

HRID 856168 reaction equation
FC(F)(F)C(O)=O.COC[O:11][CH2:12][C@:13]1([CH3:24])[O:17][C:16]2=[N:18][C:19]([N+:21]([O-:23])=[O:22])=[CH:20][N:15]2[CH2:14]1>C(Cl)Cl>[OH:11][CH2:12][C@:13]1([CH3:24])[O:17][C:16]2=[N:18][C:19]([N+:21]([O-:23])=[O:22])=[CH:20][N:15]2[CH2:14]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69480830(R)-2-methoxymethoxymethyl-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole

Product 1

HCID 26596862(r)-(2-Methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-yl)methanolYield 46.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (15 ml) was added to a solution of (R)-2-methoxymethoxymethyl-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole prepared in Example 28 (3.1 g, 13 mmol) in methylene chloride (30 ml) followed by stirring at room temperature for 25 hours. The reaction mixture was concentrated under reduced pressure. Methanol was added to the solution, and the resulting mixture was concentrated under reduced pressure. To the residue, 2-propanol was added, and the precipitates were filtered off and washed with 2-propanol to afford (R)-2-hydroxymethyl-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole (1.2 g, yield 46%) as a light yellow powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionMethanol was added to the solution
  3. concentrationthe resulting mixture was concentrated under reduced pressure
  4. additionTo the residue, 2-propanol was added
  5. filtrationthe precipitates were filtered off
  6. washwashed with 2-propanol

Sources & evidence

ORD record
ord-36a656878b96408eae646cd2201beed4
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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