Triethylamine → HCID 21094291, compound

HRID 1350089Notes

Reaction equation

HRID 1350089 reaction equation
C(N(CC)CC)C.Cl.[CH3:9][O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[CH2:17][NH:16][CH2:15][CH:14]2[CH2:21][CH2:22][NH:23][C:24](=[O:26])[CH3:25].[CH:27]([C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][CH:34]=1)=[O:28]>ClCCl>[CH:27]([C:29]1[CH:34]=[C:33]([N:16]2[CH2:15][CH:14]([CH2:21][CH2:22][NH:23][C:24](=[O:26])[CH3:25])[C:13]3[C:18](=[CH:19][CH:20]=[C:11]([O:10][CH3:9])[CH:12]=3)[CH2:17]2)[CH:32]=[CH:31][CH:30]=1)=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27343563-Formylphenylboronic acidHCID 21094293HCID 21094293, compound

Product 1

HCID 21094291HCID 21094291, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Copper acetate Cu(OAc)2 (960 mg; 5 mmol) and triethylamine (1.5 ml; 10.5 mmol) are suspended in 60 ml of dichloromethane. The compound of Example 4 (1 g; 3.5 mmol), 3-formylphenylboronic acid (1.05 g; 7 mmol) and molecular sieve are then added in succession and progressively to the solution. The reaction mixture is stirred at ambient temperature for 2 hours. The mixture is filtered, washed with water, dried over magnesium sulphate, filtered and evaporated under reduced pressure. The residue obtained is purified by chromatography on silica gel (eluant: dichloromethane with the progressive addition of methanol until the proportions 9/1 are reached) to yield the title product in the form of a yellow oil.

Workup

  1. filtrationThe mixture is filtered
  2. washwashed with water
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue obtained
  7. customis purified by chromatography on silica gel (eluant
  8. additiondichloromethane with the progressive addition of methanol until the proportions 9/1

Sources & evidence

ORD record
ord-79fe03c6615e4d18b4fde31698dd376c
Source dataset
uspto-grants-2007_05
Patent number
US07214689B2

Reaction notes

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