Hydroxylamine → tert-butyl N-[(1S)-1-(hydroxycarbamoyl)-3-(methylsulfanyl)propyl]carbamate

HRID 2040504Notes

Reaction equation

HRID 2040504 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][CH2:15][S:16][CH3:17])[C:10](OC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:18][OH:19]>O1CCOCC1.C(OCC)(=O)C>[OH:19][NH:18][C:10](=[O:11])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:14][CH2:15][S:16][CH3:17]

Participants

5

Reactant 2

HCID 787HydroxylamineHCID 11097398(S)-Methyl 2-((tert-butoxycarbonyl)amino)-4-(methylthio)butanoate

Product 1

HCID 44344516tert-butyl N-[(1S)-1-(hydroxycarbamoyl)-3-(methylsulfanyl)propyl]carbamateYield 33%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of (S)-methyl 2-(tert-butoxycarbonylamino)-4-(methylthio)butanoate (1 g, 3.8 mmol) in dioxane (10 mL) and hydroxylamine (50% in water, 10 mL) was stirred at room temperature for 2 days. The solution was diluted with ethyl acetate (200 mL). The organic layer was washed with 1N HCl, brine, and dried over sodium sulfate, filtered and concentrated to give a residue, which was purified on silica gel column (hexane:ethyl acetate, 1:1 to pure acetate) to give (S)-tert-butyl 1-(hydroxyamino)-4-(methylthio)-1-oxobutan-2-ylcarbamate as a white solid (0.33 g, 33%). MS calcd for (C10H20N2O4S+H)+: 265.1; MS found: (M+H)+=266.2, 166.2 (-Boc).

Workup

  1. washThe organic layer was washed with 1N HCl, brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a residue, which
  6. customwas purified on silica gel column (hexane:ethyl acetate, 1:1 to pure acetate)

Sources & evidence

ORD record
ord-5fdc047e60474559ab7517b94495e5e5
Source dataset
uspto-grants-2013_11
Patent number
US08580859B2

Reaction notes

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