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

HRID 250824ノート

反応式

HRID 250824 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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%

後処理

  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

出典と根拠

ORDレコード
ord-03ceecdf6d364c7ea181381f6f635724
出典データセット
uspto-grants-2011_01
特許番号
US07863332B2

反応ノート

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