4-Chlorophenyl Isocyanate → (R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-chlorophenylcarbamate

HRID 856182Notes

Reaction equation

HRID 856182 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:18][C:19]1[N:20]([CH2:27][C@:28]([OH:32])([CH3:31])[CH2:29][OH:30])[CH:21]=[C:22]([N+:24]([O-:26])=[O:25])[N:23]=1>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:10])[O:30][CH2:29][C@@:28]([OH:32])([CH3:31])[CH2:27][N:20]2[CH:21]=[C:22]([N+:24]([O-:26])=[O:25])[N:23]=[C:19]2[Cl:18])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 76934-Chlorophenyl IsocyanateHCID 8471TriethylamineHCID 16099121(R)-3-(2-Chloro-4-nitro-1H-imidazol-1-yl)-2-methylpropane-1,2-diol

Product 1

HCID 69481886(R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-chlorophenylcarbamateYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A THF solution (15 ml) of 4-chlorophenylisocyanate (1.3 g, 85 mmol) and triethylamine (0.1 ml) were added to a suspension of (R)-2-chloro-1-(2,3-dihydroxy-2-methylpropyl)-4-nitroimidazole prepared in Example 10 (1.5 g, 6.5 mmol) in THF (30 ml) followed by stirring at room temperature for 19 hours. Insoluble matters were removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=9/1) to afford (R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-chlorophenylcarbamate (2.1 g, yield 83%) as a white solid.

Workup

  1. customInsoluble matters were removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-96f878a971954b01acbb7224b8b93bd5
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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