Hydrochloric Acid → HCID 23081451, compound

HRID 856284Notes

Reaction equation

HRID 856284 reaction equation
C([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2([CH3:26])[O:19][C:18]3=[N:20][C:21]([N+:23]([O-:25])=[O:24])=[CH:22][N:17]3[CH2:16]2)[CH2:10][CH2:9]1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O.C(N(CC)CC)C.[Cl:41]C(O[CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=O.Cl>C(OCC)(=O)C.C(Cl)Cl>[ClH:41].[CH3:26][C:15]1([CH2:14][N:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][CH2:45][C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)=[O:7])[CH2:13][CH2:12]2)[O:19][C:18]2=[N:20][C:21]([N+:23]([O-:25])=[O:24])=[CH:22][N:17]2[CH2:16]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 230810802-(4-Tert-butoxycarbonylpiperazin-1-yl)methyl-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole

Product 1

HCID 23081451HCID 23081451, compoundYield 30.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of 2-(4-tert-butoxycarbonylpiperazin-1-yl)methyl-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole prepared in Example 306 (130 mg, 0.35 mmol), trifluoroacetic acid (3 ml) and methylene chloride (5 ml) was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in methylene chloride (5 ml) and added triethylamine (107.5 mg, 1.06 mmol). To the solution, benzyl chloroformate (120 mg, 0.71 mmol) was added with cooling on ice-bath followed by stirring at room temperature for 1 hour. The reaction mixture was washed with water, a saturated sodium hydrogencarbonate solution and a saturated saline solution in this order, dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/methanol=20/1) to afford a yellow oil. The oil was dissolved in ethyl acetate (5 ml). To the solution, a saturated hydrochloride solution in ethyl acetate 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)piperazin-1-carboxylate hydrochloride (46.8 mg, yield 30%) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in methylene chloride (5 ml)
  3. temperaturewith cooling on ice-bath
  4. stirringby stirring at room temperature for 1 hour
  5. washThe reaction mixture was washed with water
  6. dry with materiala saturated sodium hydrogencarbonate solution and a saturated saline solution in this order, dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (methylene chloride/methanol=20/1)
  10. customto afford a yellow oil
  11. filtrationthe precipitates were filtered off

Sources & evidence

ORD record
ord-d644948483844cd6a01d6b6487c1eb9d
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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