Benzoyl chloride → Ethyl (2S)-2-benzamido-3-(4-nitrophenyl)propanoate

HRID 2229494Notes

Reaction equation

HRID 2229494 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:18])[C@@H:6]([NH2:17])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)[CH3:3].[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C>ClCCl>[CH2:2]([O:4][C:5](=[O:18])[C@@H:6]([NH:17][C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)[CH3:3]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 6453710Ethyl 4-nitro-3-phenyl-L-alaninate monohydrochloride

Product 1

HCID 9840971Ethyl (2S)-2-benzamido-3-(4-nitrophenyl)propanoateYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-Ethyl-2-amino-3-(4-nitrophenyl)propionate hydrochloride (1.23 g, 4.47 mmol) was suspended in dichloromethane (25 mL) and to this suspension was added benzoyl chloride (0.628 g, 4.47 mmol) and triethylamine (1.36 g, 13.4 mmol). The mixture was stirred overnight at room temperature under nitrogen. The crude reaction was washed with 5% HCl, water, brine, dried (Na2SO4), concentrated and purified by flash chromatography (silica gel, 2:1 hexanes:EtOAc) to afford the title compound as a white powder (0.865 g, 57%): MS(ES+) m/e 343 [M+H]; mp 99-101° C.

Workup

  1. customThe crude reaction
  2. washwas washed with 5% HCl, water, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified by flash chromatography (silica gel, 2:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-0624cd5e1d1646b7be979e76806f3d1d
Source dataset
uspto-grants-2002_07
Patent number
US06420424B1

Reaction notes

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