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

HRID 2050347노트

반응식

HRID 2050347 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-42cbd268718341e799317f3118b2a48d
출처 데이터셋
uspto-grants-1980_04
특허 번호
US04200758

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