Potassium Carbonate → (S)-2-(3-Nitro-benzylamino)-3-phenyl-propionic acid ethyl ester

HRID 548231

Reaction equation

HRID 548231 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7]Br)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Cl.[CH2:19]([O:21][C:22](=[O:32])[C@H:23]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[NH2:24])[CH3:20]>CN(C=O)C>[CH2:19]([O:21][C:22](=[O:32])[C@@H:23]([NH:24][CH2:7][C:6]1[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH3:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 165085Ethyl L-phenylalaninate hydrochloride

Product 1

HCID 57971682(S)-2-(3-Nitro-benzylamino)-3-phenyl-propionic acid ethyl esterYield 24%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Nitrobenzyl bromide (10.0 g, 46 mmol) was dissolved in DMF (180 ml) and potassium carbonate (12.7 g, 92 mmol) added, followed by L-phenylalanine ethyl ester hydrochloride (10.6 g, 46 mmol). The reaction was stirred for 17 h at room temperature before evaporating to dryness. The residue was re-dissolved in EtOAc (150 ml) and washed with water (3×80 ml), dried (Na2SO4) filtered and concentrated to dryness. After purification by flash column chromatography (30% EtOAc/hexane) the product was obtained (3.7 g, 24% yield). LCMS purity 86%, m/z 329 [M++H]+.

Workup

  1. custombefore evaporating to dryness
  2. dissolutionThe residue was re-dissolved in EtOAc (150 ml)
  3. washwashed with water (3×80 ml)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customAfter purification by flash column chromatography (30% EtOAc/hexane) the product
  8. customwas obtained (3.7 g, 24% yield)

Sources & evidence

ORD record
ord-51a06088fd9f44be8bc7c483aca9dec4
Source dataset
uspto-grants-2011_05
Patent number
US07939666B2

Linked notes

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