Trifluoroacetic acid → HCID 23081374, compound

HRID 856368Notes

Reaction equation

HRID 856368 reaction equation
[CH3:1][C:2]1([CH2:13][N:14]2[CH2:20][CH2:19][CH2:18][N:17]([C:21]([O:23]C(C)(C)C)=[O:22])[CH2:16][CH2:15]2)[O:6][C:5]2=[N:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][N:4]2[CH2:3]1.FC(F)(F)C(O)=O.C(N(CC)CC)C.[Cl:42]C(O[CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=O.Cl.C(OCC)(=O)C>C(OCC)(=O)C.O>[ClH:42].[CH3:1][C:2]1([CH2:13][N:14]2[CH2:20][CH2:19][CH2:18][N:17]([C:21]([O:23][CH2:46][C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)=[O:22])[CH2:16][CH2:15]2)[O:6][C:5]2=[N:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][N:4]2[CH2:3]1

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 21866389Hydrogen chloride-ethyl acetateHCID 23081102HCID 23081102, compound

Product 1

HCID 23081374HCID 23081374, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of tert-butyl 4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)-homopiperazine-1-carboxylate prepared in Example 645 (250 mg, 0.655 mmol) and trifluoroacetic acid (10 ml) was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in methylene chloride (10 ml). To the solution, triethylamine (0.27 ml, 1.96 mmol) and benzyl chloroformate (0.19 ml, 1.31 mmol) were added followed by stirring at room temperature for 3 hours. To the reaction mixture, water was added, and the mixture was extracted with methylene chloride. The organic phase was dried over magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=1/1) to afford a light yellow oil. The resulting oil was dissolved in ethyl acetate. To the solution, a saturated hydrochloric acid/ethyl acetate solution was added, and the precipitates were filtered off to afford benzyl 4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)homopiperazine-1-carboxylate hydrochloride (246 mg, yield 83%) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in methylene chloride (10 ml)
  3. stirringby stirring at room temperature for 3 hours
  4. extractionthe mixture was extracted with methylene chloride
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=1/1)
  9. customto afford a light yellow oil
  10. filtrationthe precipitates were filtered off

Sources & evidence

ORD record
ord-9cb2d03436b745469fa5c2c426d448ea
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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