Triethylamine → Cyano(2,4-dioxo-1-propargyl-3-imidazolidinyl)methyl 2-(2-fluoro-4-trifluoromethylphenylamino)-3-methylbutanoate

HRID 2050347Notes

Reaction equation

HRID 2050347 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[NH:12][CH:13]([CH:17]([CH3:19])[CH3:18])[C:14]([OH:16])=[O:15].C(N(CC)CC)C.[C:27]([CH:29]([N:31]1[C:35](=[O:36])[CH2:34][N:33]([CH2:37][C:38]#[CH:39])[C:32]1=[O:40])O)#[N:28]>CCOCC>[F:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[NH:12][CH:13]([CH:17]([CH3:19])[CH3:18])[C:14]([O:16][CH:29]([C:27]#[N:28])[N:31]1[C:35](=[O:36])[CH2:34][N:33]([CH2:37][C:38]#[CH:39])[C:32]1=[O:40])=[O:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 202839832-(2-Fluoro-4-trifluoromethylphenylamino)-3-methylbutanoic acidHCID 20342650Cyano(2,4-dioxo-1-propargyl-3-imidazolidinyl)methanol

Product 1

HCID 86736952Cyano(2,4-dioxo-1-propargyl-3-imidazolidinyl)methyl 2-(2-fluoro-4-trifluoromethylphenylamino)-3-methylbutanoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To the acid chloride of 2-(2-fluoro-4-trifluoromethylphenylamino)-3-methylbutanoic acid (2.5 mmol) in ether is added 1.3 ml of triethylamine followed by the cyano(2,4-dioxo-1-propargyl-3-imidazolidinyl)methanol in 5 ml of ether, from part A above, over about 2 minutes. The reaction mixture is stirred for about 18 hours and then quenched with saturated aqueous sodium bicarbonate. The organic phase is washed with aqueous sodium bicarbonate, water and brine, dried over calcium sulfate and solvent evaporated. The crude product is chromatographed on a circular chromatograph eluting with 20% ether/hexane to give cyano(2,4-dioxo-1-propargyl-3-imidazolidinyl)methyl 2-(2-fluoro-4-trifluoromethylphenylamino)-3-methylbutanoate. (A', R is carbonyl, R' is methylene, R1 =R4 is hydrogen, R2 is 2-fluoro-4-trifluoromethylphenyl, R3 is isopropyl, R5 is cyano, R6 is 2-propynyl).

Workup

  1. customover about 2 minutes
  2. customquenched with saturated aqueous sodium bicarbonate
  3. washThe organic phase is washed with aqueous sodium bicarbonate, water and brine
  4. dry with materialdried over calcium sulfate and solvent
  5. customevaporated
  6. customThe crude product is chromatographed on a circular chromatograph
  7. washeluting with 20% ether/hexane

Sources & evidence

ORD record
ord-42cbd268718341e799317f3118b2a48d
Source dataset
uspto-grants-1980_04
Patent number
US04200758

Reaction notes

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