(2-(Dimethylamino)thiazol-4-yl)methanol → N-((2-(N,N-Dimethylamino)-4-thiazolyl)methoxycarbonyl)valine Methyl Ester

HRID 2210960Notes

Reaction equation

HRID 2210960 reaction equation
[CH3:1][N:2]([C:4]1[S:5][CH:6]=[C:7]([CH2:9][OH:10])[N:8]=1)[CH3:3].[CH3:11][O:12][C:13](=[O:22])[C@:14]([N:19]=[C:20]=[O:21])([CH:16]([CH3:18])[CH3:17])N>CN(C)C1C=CN=CC=1.ClCCl>[CH3:11][O:12][C:13](=[O:22])[C@H:14]([CH:16]([CH3:17])[CH3:18])[NH:19][C:20]([O:10][CH2:9][C:7]1[N:8]=[C:4]([N:2]([CH3:3])[CH3:1])[S:5][CH:6]=1)=[O:21]

Participants

5

Reactant 2

HCID 18758920(2-(Dimethylamino)thiazol-4-yl)methanolHCID 22845662a-Isocyanato-valine methyl ester

Product 1

HCID 10805288N-((2-(N,N-Dimethylamino)-4-thiazolyl)methoxycarbonyl)valine Methyl EsterYield 95%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 505 mg (3.19 mmol) of 2-(N,N-dimethylamino)-4-(hydroxymethyl)thiazole, 3.19 mmol of α-isocyanato-L-valine methyl ester, and 100 mg of 4-dimethylaminopyridine in 30 ml of dichloromethane was heated at reflux for 3 h. The resulting solution was allowed to cool, diluted with dichloromethane, washed sequentially with 10% citric acid, aqueous Na2CO3, and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by silica gel chromatography using 2% methanol in chloroform to provide 0.95 g (95%) of the desired compound, Rf 0.42 (4% methanol in chloroform).

Workup

  1. temperatureat reflux for 3 h
  2. temperatureto cool
  3. washwashed sequentially with 10% citric acid, aqueous Na2CO3, and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-54bc693cb38144b9b28cc0be5f57fb2f
Source dataset
uspto-grants-1995_10
Patent number
US05461067

Reaction notes

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