Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | 3a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dione | HCID 89529 | — |
| Reactant | N-[(Phenylmethoxy)carbonyl]-L-leucylglycine | HCID 6992483 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | N,N'-Dicyclohexylurea | HCID 4277 | — |
| Product | 3a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dione | HCID 89529 | — |
| Product | N-[(Phenylmethoxy)carbonyl]-L-leucylglycine | HCID 6992483 | — |
Reaction Steps
A solution of the N-hydroxy-5-norbornene-2,3-dicarboximide active ester of N-benzyloxycarbonyl-L-leucylglycine was prepared according to the general procedure of M. Fujino, et al [Chem. Pharm. Bull. Japan, 22, 1857 (1974)]. A solution of 1.27 g. of N-benzyloxycarbonylleucylglycine and 0.72 g. of N-hydroxy-5-norbornene-2,3-dicarboximide in 5 ml. of tetrahydrofuran was cooled in an ice bath and 0.83 g. of N,N'-dicyclohexylcarbodiimide was added to the cold solution together with 1 ml. of tetrahydrofuran. The reaction mixture was stirred at low temperature for 40 minutes and then at room temperature for 21/2 hours. The N,N'-dicyclohexylurea formed during the reaction was collected on a filter and washed with three 1-ml. portions of tetrahydrofuran.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04091032 |
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| Source dataset | uspto-grants-1978_05 |
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| ORD ID | ord-8687d831bb7d44aaabbd9f8b14d4f9a6 |
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| Source note | uspto-grants-1978_05 |
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