Ethanol → HCID 86609024, compound

HRID 2104464Notes

Reaction equation

HRID 2104464 reaction equation
C(O)C.[C:4]([C:6]1[CH:7]=[C:8]([CH:36]=[CH:37][CH:38]=1)[C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([C:18]([N:20]([CH3:22])[CH3:21])=[O:19])[CH2:14][C@H:13]1[NH:23][C:24]([C:26]1[S:27][C:28]2[CH2:29][N:30]([CH3:35])[CH2:31][CH2:32][C:33]=2[N:34]=1)=[O:25])=[O:10])#[N:5].[ClH:39].[NH2:40][OH:41].C(=O)([O-])O.[Na+]>C(Cl)Cl.C(N(CC)CC)C.O1CCCC1>[ClH:39].[NH2:5][C:4](=[N:40][OH:41])[C:6]1[CH:7]=[C:8]([CH:36]=[CH:37][CH:38]=1)[C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([C:18]([N:20]([CH3:21])[CH3:22])=[O:19])[CH2:14][C@H:13]1[NH:23][C:24]([C:26]1[S:27][C:28]2[CH2:29][N:30]([CH3:35])[CH2:31][CH2:32][C:33]=2[N:34]=1)=[O:25])=[O:10]

Participants

8

Reactant 4

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 57804588HCID 57804588, compound

Product 1

HCID 86609024HCID 86609024, compoundYield 56.8%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

Ethanol (5.0 mL) and tetrahydrofuran (2.0 mL) were added to the compound obtained in Example 367 (270 mg) for dissoltion, and hydroxylamine hydrochloride (114 mg) and triethylamine (230 μL) were added to the solution at room temperature. The mixture was heated under reflux for 3 hours, and saturated aqueous sodium hydrogencarbonate and methylene chloride were added to the reaction mixture to partition the mixture, followed by extracting the formed aqueous layer with methylene chloride. The extract was combined with the organic layer, and the mixture was dried over sodium sulfate anhydrate. The solvent was removed under reduced pressure. The residue was purified through silica gel column chromatography (methylene chloride:methanol=7:1), a sephadex column (methanol), and fractional reversed phase high performance liquid chromatography (acetonitrile-water-formic acid). The product was converted to a hydrochloride with 1N HCl, and subsequently, the salt was purified through use of a sephadex column (methanol), to thereby yield the title compound (175 mg) as a white solid.

Workup

  1. additionwere added to the solution at room temperature
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 3 hours
  4. customto partition the mixture
  5. extractionby extracting the formed aqueous layer with methylene chloride
  6. dry with materialthe mixture was dried over sodium sulfate anhydrate
  7. customThe solvent was removed under reduced pressure
  8. customThe residue was purified through silica gel column chromatography (methylene chloride:methanol=7:1)
  9. customsubsequently, the salt was purified through use of a sephadex column (methanol)

Sources & evidence

ORD record
ord-7021f7bb8a154b39a59c1a19ce29dfb9
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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