n-Heptyl isocyanate → Methyl 3-[3'-(1-methyl-3-heptyl-ureido)biphenyl-4-yl]propanoate

HRID 250832

반응식

HRID 250832 반응식
[CH2:1]([N:8]=[C:9]=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH3:11][NH:12][C:13]1[CH:14]=[C:15]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:21][CH:20]=2)[CH:16]=[CH:17][CH:18]=1.O1CCCC1.C(N(CC)CC)C>O>[CH3:11][N:12]([C:13]1[CH:14]=[C:15]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:21][CH:20]=2)[CH:16]=[CH:17][CH:18]=1)[C:9]([NH:8][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[O:10]

참가 물질

5

반응물 3

HCID 138341n-Heptyl isocyanateHCID 67273433Methyl 3-(3'-methylaminobiphenyl-4-yl)propanoateHCID 68616177Triethylamine tetrahydrofuran

생성물 1

HCID 67272234Methyl 3-[3'-(1-methyl-3-heptyl-ureido)biphenyl-4-yl]propanoate수율 76%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
40 °C

실험 절차

1.2 mL (7.43 mmol, 2 eq) of heptyl isocyanate are added to a solution of 1.0 g (3.7 mmol, 1 eq) of methyl 3-(3′-methylaminobiphenyl-4-yl)propanoate (obtained as in 4c) in 15 mL of a 4/1 tetrahydrofuran/triethylamine mixture. The reaction mixture is stirred for 12 hours at 40° C. The reaction is stopped by addition of 10 mL of water and then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on silica gel (70/30 heptane/ethyl acetate). 1.15 g of methyl 3-[3′-(1-methyl-3-heptyl-ureido)biphenyl-4-yl]propanoate are obtained. Yield=76%

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. customThe solvents are evaporated off
  4. customthe residue is then chromatographed on silica gel (70/30 heptane/ethyl acetate)

출처 및 근거

ORD 기록
ord-800f07e77d51499d8878a360cbebb2cd
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863332B2

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