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

HRID 250845
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HRID 250845 반응식
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]
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참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 4

HCID 167845
palladium(II) acetate
촉매
HCID 27342162-(Dicyclohexylphosphino)biphenyl촉매
HCID 962Water용매
HCID 6228Dimethylformamide용매

실험 절차

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%

후처리

  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)

출처 및 근거

ORD 기록
ord-bc61e1b7bd4c47ae861b21ec2cbae203
출처 데이터셋
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07863332B2

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