Hydrogen chloride-ethyl acetate → (2S,3R)-2-amino-3-methoxy-N,N-dimethyl-butanamide

HRID 1620712Notes

Reaction equation

HRID 1620712 reaction equation
C(OC([NH:8][C@H:9]([C:14]([N:16]([CH3:18])[CH3:17])=[O:15])[C@@H:10]([CH3:13])[O:11][CH3:12])=O)(C)(C)C.Cl.C(OCC)(=O)C>C(OCC)(=O)C>[CH3:18][N:16]([CH3:17])[C:14](=[O:15])[C@H:9]([C@@H:10]([CH3:13])[O:11][CH3:12])[NH2:8]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86678875N2-(tert-butoxycarbonyl)-N,N,O-trimethyl-L-threoninamide

Product 1

HCID 86678876(2S,3R)-2-amino-3-methoxy-N,N-dimethyl-butanamideYield 96.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N2-(tert-butoxycarbonyl)-N,N,O-trimethyl-L-threoninamide (2.02 g) in ethyl acetate (10 mL) was added 4N hydrogen chloride/ethyl acetate solution (10 mL) at room temperature. The reaction mixture was stirred at room temperature for 3 hr, and the reaction mixture was concentrated under reduced pressure. To the reaction mixture was added methanol (10 mL). To the reaction mixture was added AMBERLYST (registered trademark) A21 (1.00 g) at room temperature. The reaction mixture was stirred at room temperature for 1 hr, the insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure to give the title compound (1.20 g).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionTo the reaction mixture was added methanol (10 mL)
  3. additionTo the reaction mixture was added AMBERLYST (registered trademark) A21 (1.00 g) at room temperature
  4. stirringThe reaction mixture was stirred at room temperature for 1 hr
  5. customthe insoluble material was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-21aebf40720245edb09ad6e3babbb3fc
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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