Triethylamine → HCID 86754073, compound

HRID 1075667Notes

Reaction equation

HRID 1075667 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[CH:10][C:11]2[CH:20]=[CH:19][C:18]([O:21][CH:22]([CH3:26])[C:23](O)=[O:24])=[C:17]3[C:12]=2[CH:13]=[CH:14][CH:15]=[N:16]3)[C:2]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>C1COCC1>[CH3:29][O:30][C:31](=[O:35])[C@H:32]([CH3:34])[NH:33][C:23](=[O:24])[CH:22]([O:21][C:18]1[CH:19]=[CH:20][C:11]([CH:10]=[C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][C:2]2=[O:27])=[C:12]2[C:17]=1[N:16]=[CH:15][CH:14]=[CH:13]2)[CH3:26]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 2733257Alanine methyl ester hydrochlorideHCID 67558205HCID 67558205, compound

Product 1

HCID 86754073HCID 86754073, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[5-(2-oxindol-3-ylidenemethyl)quinol-8-yloxy]propionic acid (100 mg, 0.28 mmol), L-alanine methyl ester hydrochloride (40 mg, 0.29 mmol) and triethylamine (0.4 ml) in THF (10 ml) was added N, N'-dicyclohexylcarbodiimide (60 mg, 0.29 mmol) at room temperature under stirring. The stirring was continued for 15 h, then the mixture was filtered and the filtrate evaporated under vacuum. The residue was chromatographed on silica gel using as eluant ethylacetate methanol (9:1) to give pure title compound in 44.1% yield (55 mg).

Workup

  1. filtrationthe mixture was filtered
  2. customthe filtrate evaporated under vacuum
  3. customThe residue was chromatographed on silica gel using as eluant ethylacetate methanol (9:1)

Sources & evidence

ORD record
ord-ea9da86631ea42fdabe211ebe457b6ed
Source dataset
uspto-grants-1999_05
Patent number
US05905149

Reaction notes

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