Hydrochloric Acid → 1-Hydroxycarbamoyl-3-methylsulfanyl-propyl-amine hydrochloride (S)-2-amino-N-hydroxy-4-(methylthio)butanamide hydrochloride

HRID 2040505Notes

Reaction equation

HRID 2040505 reaction equation
[OH:1][NH:2][C:3](=[O:17])[C@@H:4]([NH:9]C(=O)OC(C)(C)C)[CH2:5][CH2:6][S:7][CH3:8].[ClH:18].O1CCOCC1>>[ClH:18].[NH2:9][C@@H:4]([CH2:5][CH2:6][S:7][CH3:8])[C:3]([NH:2][OH:1])=[O:17].[ClH:18].[OH:1][NH:2][C:3]([CH:4]([NH2:9])[CH2:5][CH2:6][S:7][CH3:8])=[O:17]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 44344516tert-butyl N-[(1S)-1-(hydroxycarbamoyl)-3-(methylsulfanyl)propyl]carbamate

Product 1

HCID 866564651-Hydroxycarbamoyl-3-methylsulfanyl-propyl-amine hydrochloride (S)-2-amino-N-hydroxy-4-(methylthio)butanamide hydrochlorideYield 80%

Procedure

To solid (S)-tert-butyl 1-(hydroxyamino)-4-(methylthio)-1-oxobutan-2-ylcarbamate (0.33 g, 1.25 mmol) was added 4 N HCl in dioxane (2 mL, 8 mmol). The mixture was stirred at room temperature for one hour, and concentrated. The residue was triturated with ether, and dried to provide 1-Hydroxycarbamoyl-3-methylsulfanyl-propyl-amine hydrochloride (S)-2-amino-N-hydroxy-4-(methylthio)butanamide hydrochloride (0.18 g, 80%). MS calcd for (C5H12N2O2S—H)+: 163.1; MS found: (M−H)+=163.0

Workup

  1. concentrationconcentrated
  2. customThe residue was triturated with ether
  3. customdried

Sources & evidence

ORD record
ord-81e1b863f9c94012962bfb94c3699e7f
Source dataset
uspto-grants-2013_11
Patent number
US08580859B2

Reaction notes

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