Hydrogen chloride-ethyl acetate → HCID 86678862, compound

HRID 1620700Notes

Reaction equation

HRID 1620700 reaction equation
C(OC([NH:8][C@H:9]([C:13]([N:15]([CH3:17])[CH3:16])=[O:14])[CH2:10][O:11][CH3:12])=O)(C)(C)C.Cl.C(OCC)(=O)C>C(OCC)(=O)C>[CH3:16][N:15]([CH3:17])[C:13](=[O:14])[C@H:9]([CH2:10][O:11][CH3:12])[NH2:8]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86678861HCID 86678861, compound

Product 1

HCID 86678862HCID 86678862, compoundYield 147.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N2-(tert-butoxycarbonyl)-N,N,O-trimethyl-L-serinamide (2.08 g) in ethyl acetate (10 mL) was is added 4N hydrogen chloride/ethyl acetate solution (10 mL) under ice-cooling. The reaction mixture was stirred at room temperature overnight, and the solvent was evaporated under reduced pressure. To a solution of the residue in methanol (20 mL) was added AMBERLYST (registered trademark) A21 (2.0 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 (1.82 g).

Workup

  1. temperaturecooling
  2. customthe solvent was evaporated under reduced pressure
  3. additionTo a solution of the residue in methanol (20 mL) was added AMBERLYST (registered trademark) A21 (2.0 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-4f63d0747d5045a9a7bb63db46b470e9
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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