Triethylamine → HCID 67811148, compound

HRID 1290026Notes

Reaction equation

HRID 1290026 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:15](=[O:16])[NH:14][C:13](=[O:17])[C:12]=2[C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]([CH2:27][CH2:28][C:29](O)=[O:30])[CH:19]=2)=[CH:3]1.C1(N=C=NC2CCCCC2)CCCCC1.Cl.[CH2:48]([O:50][C:51](=[O:55])[C@H:52]([CH3:54])[NH2:53])C.C(N(CC)CC)C>O1CCCC1>[CH3:48][O:50][C:51](=[O:55])[C@H:52]([CH3:54])[NH:53][C:29](=[O:30])[CH2:28][CH2:27][N:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:18]([C:12]2[C:13](=[O:17])[NH:14][C:15](=[O:16])[C:11]=2[C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:2]([CH3:1])[CH:3]=2)=[CH:19]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 2724356L-Alanine, ethyl ester, hydrochloride (1:1)HCID 18780298HCID 18780298, compound

Product 1

HCID 67811148HCID 67811148, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-[3-[4-(1-Methylindol-3-yl)-1H-pyrrole-2,5-dion-3-yl]-indol-1-yl)-propionic acid 272 mg (0.65 mmol) are dissolved in 3 mL anhydrous tetrahydrofuran and mixed with 145 mg (0.70 mmol) dicyclohexylcarbodiimide and a mixture of 90 mg (0.8 mmol) alanine ethyl ester hydrochloride and 85 mg triethylamine dissolved in 5 mL anhydrous tetrahydrofuran. The reaction mixture is stirred for 24 hours at ambient temperature, the solvent is then distilled off in a vacuum, the residue is taken up in 100 mL ethyl acetate, and the organic phase is washed with water. After drying over anhydrous sodium sulphate and distilling off the solvent in a vacuum, the crude product obtained is separated by thick layer chromatography (silica gel, dichloromethane/methanol=90:10%). The fraction with the RF of 0.31 is separated, the product is extracted and, after removal of the solvent in a vacuum, there are isolated 130 mg (40% of theory) of the desired product;

Workup

  1. distillationthe solvent is then distilled off in a vacuum
  2. washthe organic phase is washed with water
  3. dry with materialAfter drying over anhydrous sodium sulphate
  4. distillationdistilling off the solvent in a vacuum
  5. customthe crude product obtained
  6. customis separated by thick layer chromatography (silica gel, dichloromethane/methanol=90:10%)
  7. customThe fraction with the RF of 0.31 is separated
  8. extractionthe product is extracted
  9. customafter removal of the solvent in a vacuum, there

Sources & evidence

ORD record
ord-2012636c8d9d4210a93db1477886db0e
Source dataset
uspto-grants-1998_05
Patent number
US05750555

Reaction notes

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