4-Nitrobenzoic Acid → N-(4-Nitrobenzoyl)threonine methyl ester

HRID 1425050Notes

Reaction equation

HRID 1425050 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:10])[C@H:5]([C@@H:7]([CH3:9])[OH:8])[NH2:6].[N+:11]([C:14]1[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=1)([O-:13])=[O:12].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C>ClCCl>[CH3:2][O:3][C:4](=[O:10])[C@H:5]([C@@H:7]([CH3:9])[OH:8])[NH:6][C:18](=[O:19])[C:17]1[CH:16]=[CH:15][C:14]([N+:11]([O-:13])=[O:12])=[CH:22][CH:21]=1

Participants

7

Reactant 5

HCID 61084-Nitrobenzoic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2734893Methyl L-threoninate hydrochloride

Product 1

HCID 67548381N-(4-Nitrobenzoyl)threonine methyl esterYield 94.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dichloromethane (80 mL) was added to threonine methyl ester hydrochloride (3.39 g, 20 mmol), 4-nitrobenzoic acid (3.34 g, 20 mmol), WSC hydrochloride (3.83 g, 20 mmol), HOBt (2.87 g, 20 mmol) and N,N-diisopropylethylamine (2.58 g, 20 mmol), and the mixture was stirred at room temperature for three days. The reaction solution was washed with water and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/2, 1/1, 1/2) to obtain 5.31 g of the title compound as a colorless solid (94%).

Workup

  1. washThe reaction solution was washed with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/2, 1/1, 1/2)

Sources & evidence

ORD record
ord-a299dea2876f43038dd69c97fe4e0146
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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