Ethyl 4-[[3,5-bis(trimethylsilyl)benzoyl]amino]cinnamate → Ethyl 3-[4-[[3,5-bis(trimethylsilyl)benzoyl]amino]phenyl]propanoate

HRID 2265117Notes

Reaction equation

HRID 2265117 reaction equation
[CH3:1][Si:2]([CH3:30])([CH3:29])[C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([Si:25]([CH3:28])([CH3:27])[CH3:26])[CH:24]=1)[C:6]([NH:8][C:9]1[CH:21]=[CH:20][C:12]([CH:13]=[CH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][CH:10]=1)=[O:7].[H][H]>CO.C(OCC)(=O)C>[CH3:28][Si:25]([CH3:26])([CH3:27])[C:23]1[CH:22]=[C:5]([CH:4]=[C:3]([Si:2]([CH3:1])([CH3:30])[CH3:29])[CH:24]=1)[C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:20][CH:21]=1)=[O:7]

Participants

5

Reactant 2

HCID 68487569Ethyl 4-[[3,5-bis(trimethylsilyl)benzoyl]amino]cinnamateHCID 178418361HCID 178418361, compound

Product 1

HCID 68485079Ethyl 3-[4-[[3,5-bis(trimethylsilyl)benzoyl]amino]phenyl]propanoateYield 99.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound 17a (150 mg) was dissolved in methanol (35 ml) and ethyl acetate (35 ml). The obtained mixture was stirred for 30 minutes in a hydrogen atmosphere. After the reaction was over, the obtained reaction mixture was filtered through Cerite, and then washed with methanol. The solvent was distilled off from the filtrate, and the obtained residue was dried. Thus, Compound 20a (150 mg, quant.) was obtained as a white solid.

Workup

  1. customthe obtained reaction mixture
  2. filtrationwas filtered through Cerite
  3. washwashed with methanol
  4. distillationThe solvent was distilled off from the filtrate
  5. customthe obtained residue was dried

Sources & evidence

ORD record
ord-e5f4e8f7fcce40cbad5658a312266c25
Source dataset
uspto-grants-2010_12
Patent number
US07855300B2

Reaction notes

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