3',4'-Dimethoxycinnamic acid → HCID 67343458, compound

HRID 1673490Notes

Reaction equation

HRID 1673490 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH:12]=[CH:13][C:14]([OH:16])=O.[NH2:22][C:23]1[CH:35]=[C:34]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:33]=[CH:32][C:24]=1[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].C(=O)([O-])O.[Na+]>C(N(CC)CC)C.C(Cl)Cl.CN(C)C=O>[CH3:7][O:8][C:9]1[CH:10]=[C:11](/[CH:12]=[CH:13]/[C:14]([NH:22][C:23]2[CH:35]=[C:34]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH:33]=[CH:32][C:24]=2[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[O:16])[CH:17]=[CH:18][C:19]=1[O:20][CH3:21]

Participants

8

Reactant 4

HCID 168483',4'-Dimethoxycinnamic acidHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 58508425Tert-butyl 3-amino-[1,1'-biphenyl]-4-carboxylate

Product 1

HCID 67343458HCID 67343458, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

1.3 mL of methylene chloride, 1.3 μL of N,N-dimethylformamide and 0.031 mL of oxalyl chloride were added to 69 mg of 3,4-dimethoxycinnamic acid at room temperature sequentially and stirred at the same temperature for 1 hour. Tine reaction mixture was added to a mixed solution of 54 mg of tert-butyl 2-amino-4-phenylbenzoate, 3.7 mL of methylene chloride and 0.22 mL of triethylamine and stirred at room temperature for 2 hours. A saturated sodium hydrogen carbonate aqueous solution was added to the reaction mixture, and the organic layer was separated, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex Company, eluent; hexane; ethyl acetate=4:1] to obtain (E)-tert-butyl 2-(3-(3,4-dimethoxyphenyl)acrylamido)-4-phenylbenzoate.

Workup

  1. customTine reaction mixture
  2. stirringstirred at room temperature for 2 hours
  3. customthe organic layer was separated
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex Company, eluent; hexane; ethyl acetate=4:1]

Sources & evidence

ORD record
ord-1868690e8ed544c69026934a0346b7c4
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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