Triethylamine → (S)-methyl 2-(3-(2,4-dimethoxybenzyl)ureido)-3-methylbutanoate

HRID 2401270Notes

Reaction equation

HRID 2401270 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:10])[C@H:5]([CH:7]([CH3:9])[CH3:8])[NH2:6].C(N(CC)CC)C.[CH3:18][O:19][C:20]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:21]=1[CH2:22][N:23]=[C:24]=[O:25]>C(Cl)(Cl)Cl>[CH3:18][O:19][C:20]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:21]=1[CH2:22][NH:23][C:24]([NH:6][C@H:5]([C:4]([O:3][CH3:2])=[O:10])[CH:7]([CH3:9])[CH3:8])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 111190Methyl valinate hydrochlorideHCID 112525271-(Isocyanatomethyl)-2,4-dimethoxybenzene

Product 1

HCID 2012917(S)-methyl 2-(3-(2,4-dimethoxybenzyl)ureido)-3-methylbutanoateYield 83.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of L-valine methyl ester hydrochloride (2.6 g) and triethylamine (1.6 g) in chloroform (30 mL) was added 2,4-dimethoxybenzyl isocyanate (3.0 g), and the mixture was stirred at room temperature overnight. After the solvent was distilled off under reduced pressure, the residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate) to afford methyl N-[(2,4-dimethoxybenzyl)carbamoyl]-L-valinate (4.2 g).

Workup

  1. distillationAfter the solvent was distilled off under reduced pressure
  2. customthe residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-6c9c879013e442609e8fb4e976481494
Source dataset
uspto-grants-2014_08
Patent number
US08796272B2

Reaction notes

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