Dicyclohexylcarbodiimide → (2,4-Dioxo-5-methyl-1-propargyl-3-imidazolidinyl)methyl 2-(2-chloro-4-trifluoromethylphenylamino)-3-methylbutanoate

HRID 2050348Notes

Reaction equation

HRID 2050348 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][OH:8])[C:5](=[O:9])[CH:4]([CH3:10])[N:3]1[CH2:11][C:12]#[CH:13].[Cl:14][C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:16]=1[NH:25][C@H:26]([C:30](O)=[O:31])[CH:27]([CH3:29])[CH3:28].CN(C1C=CC=CN=1)C.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C)C=O>[Cl:14][C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:16]=1[NH:25][CH:26]([CH:27]([CH3:29])[CH3:28])[C:30]([O:8][CH2:7][N:6]1[C:5](=[O:9])[CH:4]([CH3:10])[N:3]([CH2:11][C:12]#[CH:13])[C:2]1=[O:1])=[O:31]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 156536L-Valine, N-[2-chloro-4-(trifluoromethyl)phenyl]-HCID 20342664(2,4-Dioxo-5-methyl-1-propargyl-3-imidazolidinyl)methanol

Product 1

HCID 20342656(2,4-Dioxo-5-methyl-1-propargyl-3-imidazolidinyl)methyl 2-(2-chloro-4-trifluoromethylphenylamino)-3-methylbutanoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (2,4-dioxo-5-methyl-1-propargyl-3-imidazolidinyl)methanol (1.8 mmol), N-(2-chloro-4-trifluoromethylphenyl)valine (2.0 mmol) and dimethylaminopyridine (0.65 mmol) in 20 ml of methylene chloride and 2 ml of dimethylformamide is added N,N'-dicyclohexylcarbodiimide (2.0 mmol). The reaction mixture is stirred, under nitrogen, for two hours and then filtered and extracted with water. The aqueous phase is extracted with ether. The combined organic phases are washed with saturated aqueous sodium bicarbonate, water and saturated aqueous sodium chloride, dried over calcium sulfate and solvent evaporated. The crude product is chromatographed on a rotary chromatograph, eluting with 25% ether/hexane, to yield (2,4-dioxo-5-methyl-1-propargyl-3-imidazolidinyl)methyl 2-(2-chloro-4-trifluoromethylphenylamino)-3-methylbutanoate.

Workup

  1. filtrationfiltered
  2. extractionextracted with water
  3. extractionThe aqueous phase is extracted with ether
  4. washThe combined organic phases are washed with saturated aqueous sodium bicarbonate, water and saturated aqueous sodium chloride
  5. dry with materialdried over calcium sulfate and solvent
  6. customevaporated
  7. customThe crude product is chromatographed on a rotary chromatograph
  8. washeluting with 25% ether/hexane

Sources & evidence

ORD record
ord-9f808152bce54c8a8b2825ebae58721a
Source dataset
uspto-grants-1980_04
Patent number
US04200758

Reaction notes

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