Hydrochloric Acid → HCID 86609026, compound

HRID 2104465Notes

Reaction equation

HRID 2104465 reaction equation
[ClH:1].[C:2]([C:4]1[CH:5]=[C:6]([CH:34]=[CH:35][CH:36]=1)[C:7]([NH:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([C:16]([N:18]([CH3:20])[CH3:19])=[O:17])[CH2:12][C@H:11]1[NH:21][C:22]([C:24]1[S:25][C:26]2[CH2:27][N:28]([CH3:33])[CH2:29][CH2:30][C:31]=2[N:32]=1)=[O:23])=[O:8])#[N:3].Cl.[CH3:38][O:39][NH2:40].C(=O)([O-])O.[Na+]>C(O)C.CO.C(Cl)Cl.C(N(CC)CC)C>[ClH:1].[NH2:3][C:2](=[N:40][O:39][CH3:38])[C:4]1[CH:5]=[C:6]([CH:34]=[CH:35][CH:36]=1)[C:7]([NH:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([C:16]([N:18]([CH3:19])[CH3:20])=[O:17])[CH2:12][C@H:11]1[NH:21][C:22]([C:24]1[S:25][C:26]2[CH2:27][N:28]([CH3:33])[CH2:29][CH2:30][C:31]=2[N:32]=1)=[O:23])=[O:8]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 57804588HCID 57804588, compound

Product 1

HCID 86609026HCID 86609026, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Saturated HCl in ethanol (30 mL) was added to the compound obtained in Example 367 (300 mg) at room temperature. The mixture was stirred for 2 days and then concentrated under reduced pressure, thereby yielding a pale yellow solid. The solid was dissolved in methanol (10 mL). O-Methylhydroxylamine hydrochloride (1.01 g) and triethylamine (1.69 mL) were added to the solution at room temperature. The mixture was stirred for 2 hours, and methylene chloride and saturated aqueous sodium hydrogencarbonate were added to the reaction mixture to partition the mixture, followed by extracting the aqueous layer with methylene chloride. The extract was combined with the organic layer and then dried over sodium sulfate anhydrate, and the solvent was removed under reduced pressure. The residue was purified sequentially through silica gel medium-pressure chromatography (methylene chloride:methanol=20:1→7:1) and fractional reversed phase high performance liquid chromatography (acetonitrile-water-formic acid), and the product was treated with 1N HCl, to thereby yield the title compound (51.8 mg) as a white solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customyielding a pale yellow solid
  3. stirringThe mixture was stirred for 2 hours
  4. customto partition the mixture
  5. extractionby extracting the aqueous layer with methylene chloride
  6. dry with materialdried over sodium sulfate anhydrate
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was purified sequentially through silica gel medium-pressure chromatography (methylene chloride:methanol=20:1→7:1) and fractional reversed phase high performance liquid chromatography (acetonitrile-water-formic acid)
  9. additionthe product was treated with 1N HCl

Sources & evidence

ORD record
ord-e87801a46093426cb967e293ef641b08
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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