Ethyl 2-(benzylamino)propanoate → Methyl 4-(benzyl(1-ethoxy-1-oxopropan-2-yl)amino)butanoate

HRID 450227

Reaction equation

HRID 450227 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:6])[CH3:2].O=[C:17]([CH2:22][CH3:23])[C:18]([O:20][CH3:21])=[O:19]>ClCCCl>[CH3:21][O:20][C:18](=[O:19])[CH2:17][CH2:22][CH2:23][N:7]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH:5]([C:4]([O:3][CH2:1][CH3:2])=[O:15])[CH3:6]

Participants

4

Reactant 2

HCID 222273Ethyl 2-(benzylamino)propanoateHCID 5451272-Ketobutyric acid methyl ester

Product 1

HCID 67423852Methyl 4-(benzyl(1-ethoxy-1-oxopropan-2-yl)amino)butanoate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

2-Benzylamino-propionic acid ethyl ester (1.4 g, 6.7 mmol), methyl oxo-butanoate (1.7 g, 13.5 mmol), LEA (1.9 mL, 13.5 mmol) and NaBH(Oac)3 (2.9 g, 13.5 mmol) are taken up in 1,2-DCE (35 mL) and stirred at rt for 4 h. The reaction is partitioned between DCM and saturated aqueous NaHCO3. The organic layer is removed, dried over anhydrous Na2SO4, and concentrated in vacuo. The crude residue is used without further purification. MS (ESI) m/z 308.3 (M+1).

Workup

  1. customThe reaction is partitioned between DCM and saturated aqueous NaHCO3
  2. customThe organic layer is removed
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude residue is used without further purification

Sources & evidence

ORD record
ord-706097fb77c34eac9dcbb05dff386e10
Source dataset
uspto-grants-2013_07
Patent number
US08486954B2

Linked notes

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