Sodium hydride → (R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl 4-(4-chlorobenzyl)piperazine-1-carboxylate

HRID 856204Notes

Reaction equation

HRID 856204 reaction equation
[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][C@@:17]([OH:29])([CH3:28])[CH2:18][N:19]3[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[N:21]=[C:20]3Cl)=[O:14])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[H-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][C@:17]3([CH3:28])[O:29][C:20]4=[N:21][C:22]([N+:24]([O-:26])=[O:25])=[CH:23][N:19]4[CH2:18]3)=[O:14])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 69480796(R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-(4-chlorobenzyl)piperazine-1-carboxylate

Product 1

HCID 69479708(R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl 4-(4-chlorobenzyl)piperazine-1-carboxylateYield 28%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution of (R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-(4-chlorobenzyl)piperazine-1-carboxylate prepared in Example 90 (1.82 g, 3.85 mmol) in DMF (10 ml), sodium hydride (0.31 g, 7.70 mmol) was added followed by stirring for 1 hour with cooling on ice-bath. To the reaction mixture, ice-water was added, and the precipitates were filtered off and washed with isopropanol to afford (R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl 4-(4-chlorobenzyl)piperazine-1-carboxylate (0.46 g, yield 28%) as a light yellow solid.

Workup

  1. temperaturewith cooling on ice-bath
  2. filtrationthe precipitates were filtered off
  3. washwashed with isopropanol

Sources & evidence

ORD record
ord-880b8b0a412c47488f37b10f2b67c0f1
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

Loading…