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

HRID 539011Notes

Reaction equation

HRID 539011 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C@@H:4]([N:8]=[C:9]=[O:10])[CH:5]([CH3:7])[CH3:6].[CH3:12][O:13][C:14]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=1[CH2:22][NH2:23].CCN(CC)CC>C(Cl)(Cl)Cl>[CH3:12][O:13][C:14]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=1[CH2:22][NH:23][C:9](=[O:10])[NH:8][C@@H:4]([CH:5]([CH3:7])[CH3:6])[C:3]([O:2][CH3:1])=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5972502,4-DimethoxybenzylamineHCID 10397066Methyl (S)-(-)-2-Isocyanato-3-methylbutyrate

Product 1

HCID 2012917(S)-methyl 2-(3-(2,4-dimethoxybenzyl)ureido)-3-methylbutanoate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of (S)-methyl-2-isocyanato-3-methylbutanoate (4.46 mL, 29.9 mmol) in CHCl3 (50 mL) was added drop-wise to a solution of (2,4-dimethoxyphenyl)-methanamine (5.00 g, 29.9 mmol) and NEt3 (8.34 mL, 59.8 mmol) in CHCl3 (100 mL) at ambient temperature. The resultant mixture was heated at 60° C. for 12 hours, then cooled to ambient temperature. The cooled reaction mixture was concentrated to provide (S)-methyl 2-(3-(2,4-dimethoxybenzyl)ureido)-3-methylbutanoate as a white solid, 1.25 g (13%). LCMS (APCI+) m/z 325 [M+H]+.

Workup

  1. customThe cooled reaction mixture
  2. concentrationwas concentrated

Sources & evidence

ORD record
ord-0d085a4da4e146a282afa81960bb84fd
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

Loading…