Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethylmorpholine | HCID 7525 | — |
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | Cyclopentanecarboxylic acid | HCID 18840 | — |
| Reactant | Benzyl 3-phenyl-L-alaninate | HCID 736312 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 14181528 | HCID 14181528 | — |
Reaction Steps
A cool solution of 2.06 gm of dicyclohexylcarbodiimide in 10 ml of dichloromethane was added to a solution of 1.4114 gm of cyclopentanecarboxylic acid in 5 ml of dichloromethane at -5° C. It was followed by the addition of 4.28 gm of phenylalanine benzyl ester touluenesulfonate salt in 10 ml of DMF which was neutralized with 1.36 ml of N-ethyl morpholine. The reaction mixture was stirred at 0° C. for one hour and then at room temperature for three hours. Dicyclohexylurea was removed by filtration and 50 ml of ethyl acetate was added to the filtrate. The organic phase was washed until neutral, dried over anhydrous MgSO4 and filtered. The solvent was removed with a rotary evaporator. The residue was crystallized from isopropanol and hexane yielding 2.35 gm of white crystals having a melting point of 88°-89° C. Elemental analysis of these crystals yielded the following.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04692458 |
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| Source dataset | uspto-grants-1987_09 |
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| ORD ID | ord-ad273bef0e71432c9a91ed13fc17754d |
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| Source note | uspto-grants-1987_09 |
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