Water → (R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl N-methyl-N-(4-trifluoromethoxyphenyl)carbamate

HRID 856186Notes

Reaction equation

HRID 856186 reaction equation
[H-].[Na+].[CH3:3][N:4]([C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=1)[C:5](=[O:21])[O:6][CH2:7][C@@:8]([OH:20])([CH3:19])[CH2:9][N:10]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[N:12]=[C:11]1Cl.O.C(OCC)(=O)C>CN(C=O)C>[CH3:3][N:4]([C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=1)[C:5](=[O:21])[O:6][CH2:7][C@:8]1([CH3:19])[O:20][C:11]2=[N:12][C:13]([N+:15]([O-:17])=[O:16])=[CH:14][N:10]2[CH2:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 69481240(R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl N-methyl-N-(4-trifluoromethoxyphenyl)carbamate

Product 1

HCID 69481158(R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl N-methyl-N-(4-trifluoromethoxyphenyl)carbamateYield 71.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.48 g, 11.9 mmol) was added to a solution of (R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl N-methyl-N-(4-trifluoromethoxyphenyl)carbamate prepared in Example 76 (4.50 g, 9.94 mmol) in DMF (13.5 ml) with cooling on ice-bath followed by stirring at room temperature for 1 hour. Water and ethyl acetate were added to the reaction mixture, and the precipitates were filtered off. The precipitates were recrystallized from isopropanol to afford (R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl N-methyl-N-(4-trifluoromethoxyphenyl)carbamate (2.95 g, yield 71%) as a light yellow solid.

Workup

  1. temperaturewith cooling on ice-bath
  2. filtrationthe precipitates were filtered off
  3. customThe precipitates were recrystallized from isopropanol

Sources & evidence

ORD record
ord-c3499a8453634d3e8fa24debe4673d33
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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