Triethylamine → HCID 86754074, compound

HRID 1075671Notes

Reaction equation

HRID 1075671 reaction equation
[Na+].[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[CH:11][C:12]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]([O-:26])=O)=[C:18]3[C:13]=2[CH:14]=[CH:15][CH:16]=[N:17]3)[C:3]1=[O:27].Cl.[CH3:29][O:30][C:31](=[O:35])[C@H:32]([CH3:34])[NH2:33].C(N(CC)CC)C.C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C>[CH3:29][O:30][C:31](=[O:35])[C@H:32]([CH3:34])[NH:33][C:24](=[O:26])[CH2:23][O:22][C:19]1[CH:20]=[CH:21][C:12]([CH:11]=[C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[NH:2][C:3]2=[O:27])=[C:13]2[C:18]=1[N:17]=[CH:16][CH:15]=[CH:14]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 2733257Alanine methyl ester hydrochlorideHCID 131721271HCID 131721271, compound

Product 1

HCID 86754074HCID 86754074, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[5-(2-oxindol-3-ylidenemethyl)quinol-8-yloxy] acetic acid sodium salt (120 mg, 0.33 mmol), L-alanine methyl ester hydrochloride (100 mg, 0.72 mmol) and triethylamine (0.07 ml) in DMF (10 ml) was added at room temperature N,N'-dicyclohexylcarbodiimide (100 mg, 0.48 mmol) and the stirring was continued overnight. The reaction mixture was filtered and the filtrate concentrated under reduced pressure. The oily residue was taken up in dichloromethane, the organic phase washed 3 times with water, dried over sodium sulfate and concentrated under reduced pressure. The residue was chromatographed on silica gel using as eluant ethyl acetate/methanol (95:5) to give pure title compound in 70% yield (100 mg). C24H21N3O5 calcd: C66.81 H4.91 N9.74; found: C66.55 H4.56 N9.65; MS m/z 431.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. washthe organic phase washed 3 times with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was chromatographed on silica gel using as eluant ethyl acetate/methanol (95:5)

Sources & evidence

ORD record
ord-fa938a9af41d46d0bfd73b08468b7631
Source dataset
uspto-grants-1999_05
Patent number
US05905149

Reaction notes

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