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Acetic Acid → 3-[3'-(3-Heptyl-1-methylureido)-2-methylbiphenyl-4-yl]propanoic acid

HRID 250863
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HRID 250863 반응식
[OH-].[Na+].[CH3:3][N:4]([C:17]1[CH:18]=[C:19]([C:23]2C=CC(CCC(OCC)=O)=[CH:25][CH:24]=2)[CH:20]=[CH:21][CH:22]=1)[C:5]([NH:7][CH2:8][CH2:9][CH2:10][C:11]1C=C[CH:14]=[CH:13][CH:12]=1)=[O:6].O.[C:37]([OH:40])(=[O:39])[CH3:38].O1[CH2:45][CH2:44][CH2:43][CH2:42]1.[CH3:46]O>>[CH2:8]([NH:7][C:5](=[O:6])[N:4]([C:17]1[CH:18]=[C:19]([C:23]2[CH:24]=[CH:25][C:45]([CH2:46][CH2:38][C:37]([OH:40])=[O:39])=[CH:44][C:43]=2[CH3:42])[CH:20]=[CH:21][CH:22]=1)[CH3:3])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 5

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 67272529Ethyl 3-{3'-[1-methyl-3-(3-phenylpropyl)ureido]biphenyl-4-yl}propanoate

생성물 1

HCID 117185193-[3'-(3-Heptyl-1-methylureido)-2-methylbiphenyl-4-yl]propanoic acid수율 55%

실험 절차

100 mg (2.5 mmol, 3.2 eq) of sodium hydroxide are added to a solution of 348 mg (0.78 mmol, 1 eq) of ethyl 3-{3′-[1-methyl-3-(3-phenylpropyl)ureido]biphenyl-4-yl}propanoate in 6 ml of a tetrahydrofuran/methanol mixture (8/2). The reaction mixture is stirred at room temperature for 12 hours. The reaction medium is hydrolyzed with water, acidified with acetic acid solution and extracted with ethyl acetate. The organic phases are combined, washed with sodium chloride solution and dried over sodium sulfate. The solvent is evaporated off and the residual oil is chromatographed on silica (7/3 to 1/1 heptane/ethyl acetate). 180 mg of 3-[3′-(3-heptyl-1-methylureido)-2-methylbiphenyl-4-yl]propanoic acid are obtained in the form of a tacky solid. Yield=55%

후처리

  1. extractionextracted with ethyl acetate
  2. washwashed with sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customThe solvent is evaporated off
  5. customthe residual oil is chromatographed on silica (7/3 to 1/1 heptane/ethyl acetate)

출처 및 근거

ORD 기록
ord-6f40237e50844070b072f73b0b73b058
출처 데이터셋
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07863332B2

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