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Potassium Phosphate, Tribasic → methyl(E)-3-[3'-(3-heptyl-1-methylureido)-2-hydroxybiphenyl-4-yl]acrylate

HRID 250845
ノート
印刷プレビュー

反応式

HRID 250845 の反応式
C([O:8][C:9]1[CH:10]=[C:11](/[CH:16]=[CH:17]/[C:18]([O:20][CH3:21])=[O:19])[CH:12]=[CH:13][C:14]=1I)C1C=CC=CC=1.[CH2:22]([NH:29][C:30](=[O:48])[N:31]([CH3:47])[C:32]1[CH:37]=[CH:36][CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH:33]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1>[CH2:22]([NH:29][C:30](=[O:48])[N:31]([C:32]1[CH:37]=[C:36]([C:14]2[CH:13]=[CH:12][C:11](/[CH:16]=[CH:17]/[C:18]([O:20][CH3:21])=[O:19])=[CH:10][C:9]=2[OH:8])[CH:35]=[CH:34][CH:33]=1)[CH3:47])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 595749253-Heptyl-1-methyl-1-[3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl]ureaHCID 66971542methyl(E)-3-(3-benzyloxy-4-iodophenyl)acrylate

生成物 1

HCID 67273468methyl(E)-3-[3'-(3-heptyl-1-methylureido)-2-hydroxybiphenyl-4-yl]acrylate収率 118.9%

試薬・触媒・溶媒 4

HCID 167845
palladium(II) acetate
触媒
HCID 27342162-(Dicyclohexylphosphino)biphenyl触媒
HCID 962Water溶媒
HCID 6228Dimethylformamide溶媒

実験手順

A solution of 4.6 g (11.67 mmol, 1 eq) of methyl (E)-3-(3-benzyloxy-4-iodophenyl)acrylate, 4.8 g (12.83 mmol, 1.1 eq) of 3-heptyl-1-methyl-1-[3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl]urea (prepared as in Example 1e) in 18 ml of dimethylformamide+3 mL of 2M potassium phosphate solution, in the presence of 128 mg (5 mol %) of palladium acetate and 408 mg (10 mol %) of 2-(dicyclohexylphosphino)biphenyl is stirred at 80° C. for 5 hours. The reaction medium is hydrolyzed in water and then extracted with ethyl acetate. The organic phases are washed with saturated sodium chloride solution and dried over sodium sulfate. The solvents are evaporated off and the oil obtained is chromatographed on silica (7/3 heptane/ethyl acetate). 5.89 g of methyl (E)-3-[3′-(3-heptyl-1-methylureido)-2-hydroxybiphenyl-4-yl]acrylate are obtained in oil form. Yield=98%

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic phases are washed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customThe solvents are evaporated off
  5. customthe oil obtained
  6. customis chromatographed on silica (7/3 heptane/ethyl acetate)

出典と根拠

ORDレコード
ord-bc61e1b7bd4c47ae861b21ec2cbae203
出典データセット
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07863332B2

反応ノート

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