Dimethylformamide → HCID 69480649, compound

HRID 856235Notes

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

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of (R)-2-chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazole prepared in Example 12 (500 mg, 2.3 mmol), N-methylbenzylamine (334 mg, 2.76 mmol) and DMF (2.5 ml) was stirred at 60° C. for 9 hours. The reaction mixture was allowed to return to room temperature and added water followed by extraction with ethyl acetate twice. The organic phases were combined, washed with water three times, and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1) to afford (S)-1-[2-hydroxy-3-(N-methyl-N-benzylamino)-2-methylpropyl]-2-chloro-4-nitroimidazole (712 mg, yield 91%) as a yellow oil.

Workup

customto return to room temperature
extractionfollowed by extraction with ethyl acetate twice
washwashed with water three times
dry with materialdried over sodium sulfate
filtrationAfter filtration
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record: ord-6f39515c25f544ddb7bcb9e833a9d5a7
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07262212B2

Reaction notes

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