Hydroxyamine hydrochloride → tert-butyl (3Z,4R)-3-hydroxyimino-4-(phenylmethoxycarbonylaminomethyl)pyrrolidine-1-carboxylate

HRID 639123Notes

Reaction equation

HRID 639123 reaction equation
O=[C:2]1[C@H:6]([CH2:7][NH:8][C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:5][N:4]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:3]1.Cl.[NH2:27][OH:28].C([O-])(=O)C.[Na+]>CO>[OH:28]/[N:27]=[C:2]1\[CH2:3][N:4]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:5][C@H:6]\1[CH2:7][NH:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 590262121,1-Dimethylethyl(4r)-3-oxo-4-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-pyrrolidinecarboxylate

Product 1

HCID 87503005tert-butyl (3Z,4R)-3-hydroxyimino-4-(phenylmethoxycarbonylaminomethyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve 1,1-dimethylethyl(4R)-3-oxo-4-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-pyrrolidinecarboxylate (0.87 g, 2.49 mmol) in 5:1 MeOH/H O (10 mL). Add in hydroxylamine HCl (0.177 g, 2.54 mmol) and sodium acetate (2.04 g, 24.9 mmol). The mixture was heated to reflux and allowed to stir 3 hours. After the reaction was complete the solution was concentrated under reduced pressure and extracted with CHCl3 (3×). The organic layer was washed with 0.5 M HCl and brine. The solution was dried over Na2SO4, and evaporated to yield an oil. (0.90 g, quant). LCMS: m/z 364.6 (MH+).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. concentrationwas concentrated under reduced pressure
  4. extractionextracted with CHCl3 (3×)
  5. washThe organic layer was washed with 0.5 M HCl and brine
  6. dry with materialThe solution was dried over Na2SO4
  7. customevaporated
  8. customto yield an oil

Sources & evidence

ORD record
ord-624614bd68fc4695921a80f9ec29808d
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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