Ethyl bromoacetate → (s)-[But-3-enyl-(1-phenyl-ethyl)-amino]-acetic acid ethyl ester

HRID 222492

Reaction equation

HRID 222492 reaction equation
[CH2:1]([NH:5][C@H:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:7])[CH2:2][CH:3]=[CH2:4].C([O-])([O-])=O.[K+].[K+].[CH2:20]([O:22][C:23](=[O:26])[CH2:24]Br)[CH3:21]>CN(C=O)C.CCOCC>[CH2:20]([O:22][C:23](=[O:26])[CH2:24][N:5]([CH2:1][CH2:2][CH:3]=[CH2:4])[C@H:6]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH3:7])[CH3:21]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 10559173But-3-enyl-((S)-1-phenyl-ethyl)-amine

Product 1

HCID 10956339(s)-[But-3-enyl-(1-phenyl-ethyl)-amino]-acetic acid ethyl esterYield 94.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of But-3-enyl-((S)-1-phenyl-ethyl)-amine (6.37 g, 36.4 mmol) in 150 mL of DMF at 0° C. is added K2CO3 (10.0 g, 72.8 mmol) in small portions. After stirring at 0° C. for 10 min, ethylbromoacetate (8.35 g, 54.6 mmol) is added slowly. The reaction mixture, a white suspension, is stirred at r.t. overnight/16 hrs. The solution is diluted with 200 mL of ether, and washed with 3×100 ml of water. The crude product is purified by chromatography (hexane/CH2Cl2: 50/50) to give a pale liquid (8.5 g, 94.5%). (NMR and MS data confirmed, U-4117-58).

Workup

  1. stirringThe reaction mixture, a white suspension, is stirred at r.t. overnight/16 hrs
  2. washwashed with 3×100 ml of water
  3. customThe crude product is purified by chromatography (hexane/CH2Cl2: 50/50)

Sources & evidence

ORD record
ord-37ff033ca438404fbc0d26488debbf54
Source dataset
uspto-grants-2012_06
Patent number
US08207183B2

Linked notes

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