Pyridine → 2-[(E)-hydroxyiminomethyl]-6-phenylmethoxy-1,6-diazabicyclo[3.2.1]octan-7-one

HRID 515594Notes

Reaction equation

HRID 515594 reaction equation
[CH2:1]([O:8][N:9]1[C:15](=[O:16])[N:14]2[CH2:17][C@H:10]1[CH2:11][CH2:12][C@H:13]2[CH:18]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:21][OH:22].N1C=CC=CC=1>CCO>[CH2:1]([O:8][N:9]1[C:15](=[O:16])[N:14]2[CH2:17][CH:10]1[CH2:11][CH2:12][CH:13]2/[CH:18]=[N:21]/[OH:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 72204975(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbaldehyde

Product 1

HCID 898717762-[(E)-hydroxyiminomethyl]-6-phenylmethoxy-1,6-diazabicyclo[3.2.1]octan-7-oneYield 42.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbaldehyde (510 mg, 1.96 mmol), hydroxylamine hydrochloride (158 mg, 2.27 mmol) and pyridine (621 mg, 7.85 mmol) in EtOH (15 mL) was stirred at rt for 2 hrs. The reaction mixture was then concentrated and the residue was diluted with DCM (25 mL), washed with water (3×), saturated sodium chloride, dried over Na2SO4 and concentrated. The residue was purified by silica gel column chromatography (gradient elution 3:1 to 3:2 petroleum ether/EtOAc) to afford (E)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbaldehyde oxime (228 mg, 42%) as a white solid. ESI-MS (EI+, m/z): 276 [M+H]+.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. additionthe residue was diluted with DCM (25 mL)
  3. washwashed with water (3×), saturated sodium chloride
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (gradient elution 3:1 to 3:2 petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-c68ce389947c480a8dfee21a509fe5cf
Source dataset
uspto-grants-2015_08
Patent number
US09108966B2

Reaction notes

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