Potassium Hydroxide → N-(t-butoxycarbonyl)-O-ethyl-N-methyl-3-oxoserine

HRID 1519657Notes

Reaction equation

HRID 1519657 reaction equation
[OH-].[K+].[C:3]([O:7][C:8]([N:10]([CH:12]([C:18]([O:20]CC)=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH3:11])=[O:9])([CH3:6])([CH3:5])[CH3:4]>C(O)C>[C:3]([O:7][C:8]([N:10]([CH3:11])[C@H:12]([C:18]([OH:20])=[O:19])[C:13](=[O:14])[O:15][CH2:16][CH3:17])=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86679244Diethyl [(t-butoxycarbonyl)(methyl)amino]propanedioate2×

Product 1

HCID 86679248N-(t-butoxycarbonyl)-O-ethyl-N-methyl-3-oxoserine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

An ethanol solution (4.0 mL) of potassium hydroxide (0.19 g) prepared under ice cooling was added to an ethanol (2.0 mL) solution of diethyl [(t-butoxycarbonyl)(methyl)amino]propanedioate (Intermediate 3-1, 1.0 g), and the mixture was stirred for 23 hours at room temperature. The reaction mixture was concentrated under reduced pressure, and a 1.0 mol/L-sodium hydrogen carbonate aqueous solution was added, followed by extracting the mixture with ethyl acetate. The aqueous layer was cooled with iced water, and potassium hydrogen sulfate was added to adjust it to pH 2, followed by extracting the mixture with chloroform. The extract was dried over anhydrous sodium sulfate, and the desiccant was filtered out. Then, the solvent was distilled off under reduced pressure to obtain N-(t-butoxycarbonyl)-O-ethyl-N-methyl-3-oxoserine (Intermediate 7-1, light yellow oil) (0.26 g, 29%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiona 1.0 mol/L-sodium hydrogen carbonate aqueous solution was added
  3. extractionby extracting the mixture with ethyl acetate
  4. temperatureThe aqueous layer was cooled with iced water, and potassium hydrogen sulfate
  5. additionwas added
  6. extractionby extracting the mixture with chloroform
  7. dry with materialThe extract was dried over anhydrous sodium sulfate
  8. filtrationthe desiccant was filtered out
  9. distillationThen, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-8e104b00e4ae4ebdae33260dd9063fbf
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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