Potassium Carbonate → Methyl-4-(1-methoxycarbonylpropylamino)butyrate

HRID 2197657Notes

Reaction equation

HRID 2197657 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9](=[O:14])[CH2:10][CH2:11][CH2:12][NH2:13].[CH3:15][O:16][C:17](=[O:22])[C@H:18](Br)[CH2:19][CH3:20]>C(#N)C>[CH3:7][O:8][C:9](=[O:14])[CH2:10][CH2:11][CH2:12][NH:13][CH:18]([C:17]([O:16][CH3:15])=[O:22])[CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18614Methyl 4-aminobutanoateHCID 7000150methyl (2R)-2-bromobutanoate

Product 1

HCID 72347541Methyl-4-(1-methoxycarbonylpropylamino)butyrateYield 98.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of potassium carbonate (19 g, 138 mmol, 5 equiv.) and methyl-4-aminobutyrate (IVc) (8.5 g, 55.3 mmol, 2 equiv.) in acetonitrile (70 ml, 14 vol.) is added methyl-(R)-2-bromobutyrate (IIf) (5 g, 27.6 mmol, 1 equiv.). The suspension is stirred at 40° C. for 19 hours. The mixture is then filtered and the cake is rinsed with 50 ml of acetonitrile. The filtrate is concentrated to dryness under reduced pressure and the residue is dissolved in isopropylactetate. The resulting organic layer is washed with 60 ml of water and is concentrated under vacuum to afford methyl-4-(1-methoxycarbonylpropylamino)butyrate (VIa) as a colourless oil (5.91 g, 27.2 mmol, 98%).

Workup

  1. filtrationThe mixture is then filtered
  2. washthe cake is rinsed with 50 ml of acetonitrile
  3. concentrationThe filtrate is concentrated to dryness under reduced pressure
  4. dissolutionthe residue is dissolved in isopropylactetate
  5. washThe resulting organic layer is washed with 60 ml of water
  6. concentrationis concentrated under vacuum

Sources & evidence

ORD record
ord-d2c1c5b64fa3475db82c08784a4815cd
Source dataset
uspto-grants-2012_12
Patent number
US08338621B2

Reaction notes

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