Acetonitrile → Ethyl 3-(dibenzylamino)propanoate

HRID 44758Notes

Reaction equation

HRID 44758 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Cl.[CH2:8]([O:10][C:11](=[O:15])[C@H:12]([CH3:14])N)[CH3:9].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:24](#[N:26])[CH3:25]>>[CH2:16]([N:26]([CH2:24][C:25]1[CH:21]=[CH:22][CH:17]=[CH:18][CH:19]=1)[CH2:14][CH2:12][C:11]([O:10][CH2:8][CH3:9])=[O:15])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 2724356L-Alanine, ethyl ester, hydrochloride (1:1)

Product 1

HCID 44791227Ethyl 3-(dibenzylamino)propanoate

Procedure

Sodium carbonate (21.1 g, 199 mmol) was added to a suspension of fl-alanine ethyl ester hydrochloride (10.2 g, 66.4 mmol) and benzyl bromide (16.2 mL, 136 mmol) in acetonitrile (265 mL). The reaction mixture was stirred at ambient temperature overnight and then filtered through a layer of CELITE filter aid. The filter cake was rinsed with acetonitrile (100 mL). The filtrate was concentrated under reduced pressure to provide 20.28 g of ethyl 3-dibenzylaminopropionate as a pale yellow oil.

Workup

  1. filtrationfiltered through a layer of CELITE
  2. filtrationfilter aid
  3. washThe filter cake was rinsed with acetonitrile (100 mL)
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d674fba9e1e44c9fab3bae00d59fca65
Source dataset
uspto-grants-2013_09
Patent number
US08541438B2

Reaction notes

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