HuagongsheHuagongshe Chemistry Print Report · For research reference only
L-(+)-Cysteine → HCID 56619774, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | L-(+)-Cysteine | HCID 5862 | — |
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | Di-tert-butyl dicarbonate | HCID 90495 | — |
| Reactant | S-(2-Aminoethyl)-L-cysteine | HCID 99558 | — |
| Reactant | L-Proline 1,1-dimethylethyl ester | HCID 6453108 | — |
| Reactant | Benzyl (2-iodoethyl)carbamate | HCID 11301181 | — |
| Product | HCID 56619774 | HCID 56619774 | — |
Reaction Steps
S-Benzyloxycarbonylaminoethyl-L-cysteine is prepared from benzyloxycarbonyl-2-iodoethylamine and L-cysteine by the method of H. Lindley (Austral. J. Chem., 12, 296,1959). The α-amino group is protected with tert-butoxycarbonyl using di-tert-butyl dicarbonate. The resulting fully protected S-2-aminoethyl-L-cysteine is condensed with L-proline-tert-butyl ester in the presence of N,N'-dicyclohexylcarbodiimide. This intermediate is readily purified by medium pressure liquid chromatography on silica in ethyl acetate/hexane (1:1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04512979 |
| Source dataset | uspto-grants-1985_04 |
| ORD ID | ord-d9b30692782a43ccb4f4d238bdfb0a25 |
| Source note | uspto-grants-1985_04 |