Dimethylformamide → HCID 69635160, compound

HRID 856297Notes

Reaction equation

HRID 856297 reaction equation
[Cl:1][C:2]1[N:3]([CH2:10][C@@:11]2([CH3:14])[CH2:13][O:12]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[N:15]1([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.CN(C=O)C>O>[Cl:1][C:2]1[N:3]([CH2:10][C@@:11]([OH:12])([CH3:14])[CH2:13][N:18]2[CH2:17][CH2:16][N:15]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 10104781HCID 10104781, compound

Product 1

HCID 69635160HCID 69635160, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
57.5 °C

Procedure

A mixture of (S)-2-chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazole prepared in Example 18 (440 mg, 2.02 mmol), tert-butyl piperazine-1-carboxylate (414 mg, 2.22 mmol) and DMF (4 ml) was stirred at 55-60° C. for 9 hours. The reaction mixture was allowed to return to room temperature, then diluted with water (24 ml), and the solution was extracted with ethyl acetate (10 ml) twice. The organic phases were combined, washed with water (20 ml) three times and a saturated saline solution (10 ml), dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue treated with diethyl ether to afford tert-butyl (R)-4-[3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]piperazine-1-carboxylate (662 mg, yield 81%) as a light yellow powder.

Workup

  1. customto return to room temperature
  2. extractionthe solution was extracted with ethyl acetate (10 ml) twice
  3. washwashed with water (20 ml) three times
  4. dry with materiala saturated saline solution (10 ml), dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. additionthe residue treated with diethyl ether

Sources & evidence

ORD record
ord-e030abad630347468b93ef58ff355e25
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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