Water → 3-[3-Fluoro-3'-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoic acid

HRID 250824노트

반응식

HRID 250824 반응식
[OH-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N:22]([CH3:33])[C:23]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:24])[CH:17]=2)[CH:7]=[CH:8][C:9]=1[CH2:10][CH2:11][C:12]([O:14]C)=[O:13].O1CCCC1.CO.O>C(O)(=O)C>[F:3][C:4]1[CH:5]=[C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N:22]([CH3:33])[C:23]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:24])[CH:17]=2)[CH:7]=[CH:8][C:9]=1[CH2:10][CH2:11][C:12]([OH:14])=[O:13]

참가 물질

6

반응물 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 67272686Methyl 3-[3-fluoro-3'-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoate

생성물 1

HCID 580890793-[3-Fluoro-3'-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoic acid수율 44.2%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

100 mg (2.5 mmol, 8 eq) of sodium hydroxide are added to a solution of 130 mg (0.3 mmol, 1 eq) of methyl 3-[3-fluoro-3′-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoate in 3 ml of 9/1 tetrahydrofuran/methanol. The reaction mixture is stirred for 3 hours at room temperature. The reaction is stopped by addition of 10 mL of water and 1 mL of acetic acid 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). The oil obtained is crystallized from heptane/dichloromethane. 55 mg of 3-[3-fluoro-3′-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoic acid in the form of a white solid are obtained (m.p.=92-93° C.). Yield=43%

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)
  5. customThe oil obtained
  6. customis crystallized from heptane/dichloromethane

출처 및 근거

ORD 기록
ord-03ceecdf6d364c7ea181381f6f635724
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863332B2

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