2-Chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazole → Tert-butyl{4-[3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]piperazin-1-yl}carbamate

HRID 856335Notes

Reaction equation

HRID 856335 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([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>>[C:24]([O:23][C:22](=[O:28])[NH:21][N:15]1[CH2:20][CH2:19][N:18]([CH2:13][C:11]([OH:12])([CH3:14])[CH2:10][N:3]2[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=[C:2]2[Cl:1])[CH2:17][CH2:16]1)([CH3:27])([CH3:25])[CH3:26]

Participants

3

Reactant 2

HCID 159655232-Chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazoleHCID 21701658tert-Butyl piperazin-1-ylcarbamate

Product 1

HCID 91560685Tert-butyl{4-[3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]piperazin-1-yl}carbamateYield 72.6%

Procedure

Using 2-chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazole prepared in Example 6 (4.36 g, 20.0 mmol) and tert-butyl piperazin-1-ylcarbamate (4.44 g, 22.0 mmol) gave tert-butyl{4-[3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]piperazin-1-yl}carbamate (6.08 g, yield 72%) as a white powder in the same manner as in Example 365.

Sources & evidence

ORD record
ord-9dafe8f904d74c33a196de3c4eeff170
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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