Dimethylformamide → HCID 69635341, compound

HRID 856293Notes

Reaction equation

HRID 856293 reaction equation
[Cl:1][C:2]1[N:3]([CH2:10][C@@H:11]2[CH2:13][O:12]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[N:14]1([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.CN(C=O)C>O>[Cl:1][C:2]1[N:3]([CH2:10][C@@H:11]([OH:12])[CH2:13][N:17]2[CH2:16][CH2:15][N:14]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][CH2:18]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 86604801HCID 86604801, compound

Product 1

HCID 69635341HCID 69635341, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of (R)-2-chloro-1-(oxiran-2-ylmethyl)-4-nitroimidazole prepared in Example 9 (1 g, 4.91 mmol), tert-butyl piperazine-1-carboxylate (1.01 g, 5.40 mmol) and DMF (3 ml) was stirred at 70° C. for 6 hours. The reaction mixture was allowed to return to room temperature and added water (7 ml). The precipitates were filtered off, and purified by silica gel column chromatography (methylene chloride/methanol=40/1) to afford tert-butyl (S)-4-[3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxypropyl]piperazine-1-carboxylate (967 mg, 51%) as a light yellow powder.

Workup

  1. customto return to room temperature
  2. filtrationThe precipitates were filtered off
  3. custompurified by silica gel column chromatography (methylene chloride/methanol=40/1)

Sources & evidence

ORD record
ord-70a362b48cfb44559c79d3df179201ae
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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