Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | L-Alanine, ethyl ester, hydrochloride (1:1) | HCID 2724356 | — |
| Reactant | HCID 18780298 | HCID 18780298 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67811148 | HCID 67811148 | — |
Reaction Steps
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;
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05750555 |
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| Source dataset | uspto-grants-1998_05 |
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| ORD ID | ord-2012636c8d9d4210a93db1477886db0e |
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| Source note | uspto-grants-1998_05 |
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