Hydrochloric Acid → HCID 70873645, compound

HRID 2172271Notes

Reaction equation

HRID 2172271 reaction equation
C(N(CC)CC)C.[N+:8]([C:11]1[N:12]=[C:13]2[N:18]([CH:19]=1)[CH2:17][CH2:16][C@H:15]([CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[CH:24][CH:23]=1)[O:14]2)([O-:10])=[O:9].[CH:34]([O:36][CH2:37][CH2:38]Cl)=[O:35].Cl>C(Cl)Cl>[CH2:37]([O:36][C:34]([N:31]1[CH2:32][CH2:33][N:28]([C:25]2[CH:26]=[CH:27][C:22]([O:21][CH2:20][C@@H:15]3[O:14][C:13]4=[N:12][C:11]([N+:8]([O-:10])=[O:9])=[CH:19][N:18]4[CH2:17][CH2:16]3)=[CH:23][CH:24]=2)[CH2:29][CH2:30]1)=[O:35])[CH3:38]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 2467482-Chloroethyl formateHCID 70874384HCID 70874384, compound

Product 1

HCID 70873645HCID 70873645, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.31 ml) was added to a methylene chloride suspension (6 ml) of (R)-2-nitro-7-(4-piperazin-1-ylphenoxymethyl)-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (0.40 g). Subsequently, chloroethyl formate (0.11 ml) was added thereto dropwise under ice cooling, and the mixture was stirred for 14 hours while it gradually returned to room temperature. A 0.5 N hydrochloric acid aqueous solution was then added to the reaction mixture, followed by extraction with methylene chloride. After washing the organic layer with water and a saturated sodium chloride aqueous solution, the organic layer was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (methylene chloride:methanol=90:10) and recrystallized from acetone-water to afford the title compound as a pale yellow powder (0.36 g).

Workup

  1. customgradually returned to room temperature
  2. extractionfollowed by extraction with methylene chloride
  3. washAfter washing the organic layer with water
  4. dry with materiala saturated sodium chloride aqueous solution, the organic layer was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by silica gel column chromatography (methylene chloride:methanol=90:10)
  8. customrecrystallized from acetone-water

Sources & evidence

ORD record
ord-feec3f2083ed43289e79358535f38cad
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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