Potassium Carbonate → methyl-(R)-4-(1-carbamoylpropylamino)butyrate

HRID 2197660Notes

Reaction equation

HRID 2197660 reaction equation
Br[C@@H:2]([CH2:6][CH3:7])[C:3]([NH2:5])=[O:4].C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:15][O:16][C:17](=[O:22])[CH2:18][CH2:19][CH2:20][NH2:21]>C(#N)C>[CH3:15][O:16][C:17](=[O:22])[CH2:18][CH2:19][CH2:20][NH:21][C@@H:2]([C:3](=[O:4])[NH2:5])[CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27563834-Aminobutyric acid methyl ester hydrochlorideHCID 51414846(S)-2-bromobutyramide

Product 1

HCID 59650081methyl-(R)-4-(1-carbamoylpropylamino)butyrate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of (S)-2-bromobutyramide (IIh) (optical purity>98.4%; 0.25 g, 1.5 mmol), potassium carbonate (1.1 g, 8.0 mmol, 5 equiv.) and methyl-4-aminobutyrate hydrochloride (0.46 g, 3.0 mmol, 2 equiv.) is diluted in 5 ml (15 vol.) of acetonitrile and heated at 60° C. for until complete conversion. After 43 hours (GC: >90% conversion), the mixture is cooled to room temperature and filtered. The cake is rinsed with acetonitrile (20 ml) and the combined filtrates are concentrated to dryness under reduce pressure. The crude product is used directly in the subsequent step.

Workup

  1. temperaturethe mixture is cooled to room temperature
  2. filtrationfiltered
  3. washThe cake is rinsed with acetonitrile (20 ml)
  4. concentrationthe combined filtrates are concentrated to dryness

Sources & evidence

ORD record
ord-b518c0eaa8d34c00a317dac27ef069c7
Source dataset
uspto-grants-2012_12
Patent number
US08338621B2

Reaction notes

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