Triethylamine → N-((N-Methyl-N-((2-isopropyl-4-thiazolyl)methyl)amino)carbonyl)-L-valine Methyl Ester

HRID 2210948Notes

Reaction equation

HRID 2210948 reaction equation
[CH:1]([C:4]1[S:5][CH:6]=[C:7]([CH2:9][NH:10][CH3:11])[N:8]=1)([CH3:3])[CH3:2].[CH3:12][O:13][C:14](=[O:32])[C@H:15]([CH:29]([CH3:31])[CH3:30])[NH:16][C:17]([O:19]C1C=CC([N+]([O-])=O)=CC=1)=O.C(N(CC)CC)C>C1COCC1.CN(C)C1C=CN=CC=1>[CH3:12][O:13][C:14](=[O:32])[C@H:15]([CH:29]([CH3:30])[CH3:31])[NH:16][C:17]([N:10]([CH3:11])[CH2:9][C:7]1[N:8]=[C:4]([CH:1]([CH3:2])[CH3:3])[S:5][CH:6]=1)=[O:19]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 107496872-Isopropyl-4-(N-methyl)amino-methyl thiazoleHCID 15344176Methyl N-[(4-nitrophenoxy)carbonyl]-L-valinate

Product 1

HCID 10520283N-((N-Methyl-N-((2-isopropyl-4-thiazolyl)methyl)amino)carbonyl)-L-valine Methyl EsterYield 72.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 15.7 g (92 mmol) of 2-isopropyl-4-(((N-methyl)amino)methyl)thiazole in 200 ml of THF was combined with a solution of 20.5 g (69 mmol) of N-(((4-nitrophenyl)oxy)carbonyl)-L-valine methyl ester. The resulting solution was treated with 1.6 g of 4-dimethylaminopyridine and 12.9 ml (92 mmol) of triethylamine, heated at reflux for 2 h, allowed to cool, and concentrated in vacuo. The residue was taken up in CH2Cl2, washed extensively with 5% aqueous K2CO3, dried over Na2SO4, and concentrated in vacuo. The resulting product mixture was purified by silica gel chromatography using chloroform as an eluent to provide 16.3 g (54%) of the desired compound.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 h
  3. temperatureto cool
  4. concentrationconcentrated in vacuo
  5. washwashed extensively with 5% aqueous K2CO3
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe resulting product mixture was purified by silica gel chromatography

Sources & evidence

ORD record
ord-1bb104ab80e4435a9c417be9288bd4bc
Source dataset
uspto-grants-1995_10
Patent number
US05461067

Reaction notes

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