Hydroxylamine → HCID 86656467, compound

HRID 2040507Notes

Reaction equation

HRID 2040507 reaction equation
[CH3:1][C:2]([CH3:21])([CH3:20])[O:3][C:4](=[O:19])[NH:5][CH2:6][C:7](=[O:18])[NH:8][C@H:9]([C:14](OC)=[O:15])[CH2:10][CH2:11][S:12][CH3:13].[NH2:22][OH:23]>O1CCOCC1>[OH:23][NH:22][C:14](=[O:15])[C@@H:9]([NH:8][C:7](=[O:18])[CH2:6][NH:5][C:4](=[O:19])[O:3][C:2]([CH3:21])([CH3:20])[CH3:1])[CH2:10][CH2:11][S:12][CH3:13]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 86656466HCID 86656466, compound

Product 1

HCID 86656467HCID 86656467, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of (S)-methyl 12,12-dimethyl-7,10-dioxo-11-oxa-2-thia-6,9-diazatridecane-5-carboxylate (7 g, 21 mmol) in dioxane (120 mL) and hydroxylamine (50% in water, 80 mL) was stirred at room temperature for 4 hours. The solution was concentrated and extracted with ethyl acetate (200 mL). The organic layers were 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 2-(1-(hydroxyamino)-4-(methylthio)-1-oxobutan-2-ylamino)-2-oxoethylcarbamate (2 g, 28%). MS calcd for (C12H23N3O5S+H)+: 322.1; MS found: (M+H)+=322.0.

Workup

  1. concentrationThe solution was concentrated
  2. extractionextracted with ethyl acetate (200 mL)
  3. washThe organic layers were washed with 1N HCl, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a residue, which
  8. customwas purified on silica gel column (hexane:ethyl acetate, 1:1 to pure acetate)

Sources & evidence

ORD record
ord-d68ad37bbf8b483a97737a021debb975
Source dataset
uspto-grants-2013_11
Patent number
US08580859B2

Reaction notes

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