Morpholine → 4-(N-t-butoxycarbonyl-N-methyl-beta-alanyl)morpholine

HRID 847544Notes

Reaction equation

HRID 847544 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:14])[CH2:9][CH2:10][C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]([CH3:14])[CH2:9][CH2:10][C:11]([N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[O:13])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27609523-(Methylamino)propanoic acid, N-BOC protected

Product 1

HCID 197537714-(N-t-butoxycarbonyl-N-methyl-beta-alanyl)morpholineYield 99.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of N-t-butoxycarbonyl-N-methyl-β-alanine (1.02 g) and morpholine (0.48 g) in dry methylene chloride was added N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.05 g), and the mixture was stirred at ambient temperature overnight. After evaporation of the solvent, the residue was dissolved in ethyl acetate. The solution was washed with 1% citric acid aqueous solution, saturated sodium bicarbonate solution, and saturated sodium chloride solution. Then the solution was dried over magnesium sulfate and concentrated under reduced pressure to give 4-(N-t-butoxycarbonyl-N-methyl-β-alanyl)morpholine (1.36 g).

Workup

  1. customAfter evaporation of the solvent
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe solution was washed with 1% citric acid aqueous solution, saturated sodium bicarbonate solution, and saturated sodium chloride solution
  4. dry with materialThen the solution was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b65d11e65bff4b70a80e9093c36dce9d
Source dataset
uspto-grants-1992_08
Patent number
US05142048

Reaction notes

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