Potassium thiocyanate → MLS002639316

HRID 2064742Notes

Reaction equation

HRID 2064742 reaction equation
[CH2:1]([O:3][C:4](=[O:11])[C:5](=[N:9]O)[C:6](=O)[CH3:7])[CH3:2].[S-:12][C:13]#[N:14].[K+]>Cl.O.CCO.[Pd]>[CH2:1]([O:3][C:4]([C:5]1[NH:9][C:13](=[S:12])[NH:14][C:6]=1[CH3:7])=[O:11])[CH3:2]

Participants

7

Reactant 2

HCID 516872Potassium thiocyanateHCID 178472877HCID 178472877, compound

Product 1

HCID 3824588MLS002639316

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolvent2×HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Pd/C (10%, 1.00 g) is added to a solution of 2-hydroxyimino-3-oxo-butyric acid ethyl ester (62.8 mmol) in hydrochloric acid (1.25 M in EtOH, 75 mL) and the mixture is stirred at RT under a hydrogen atmosphere (4 bar) for 48 h. After filtration through celite and removal of the solvents crude 2-amino-3-oxo-butyric acid ethyl ester hydrochloride is obtained which is dissolved in a mixture of water (220 mL), EtOH (30 mL) and conc hydrochloric acid (37%, 2.5 mL). A solution of potassium thiocyanate (49.9 mmol) in water (25 mL) is added and the mixture is stirred for 2 h at reflux. By cooling in an ice bath the desired product precipitates and is collected by filtration. LC-MS: tR=0.59 min; [M+H]+=187.2.

Workup

  1. filtrationAfter filtration
  2. customthrough celite and removal of the solvents crude 2-amino-3-oxo-butyric acid ethyl ester hydrochloride
  3. customis obtained which
  4. stirringthe mixture is stirred for 2 h
  5. temperatureat reflux

Sources & evidence

ORD record
ord-e6df50f3b024417d8837be3450980d6f
Source dataset
uspto-grants-2012_10
Patent number
US08288435B2

Reaction notes

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