HuagongsheHuagongshe Chemistry Print Report · For research reference only
Isobutyl chloroformate → HCID 73944605, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Isobutyl chloroformate | HCID 62365 | — |
| Reactant | Benzyloxycarbonyl-L-phenylalanine | HCID 70878 | — |
| Reactant | L-Glutamic acid, 5-(1,1-dimethylethyl) 1-methyl ester, hydrochloride (1:1) | HCID 16218751 | — |
| Product | HCID 73944605 | HCID 73944605 | 88% |
Reaction Steps
Condensation of ZPheOH (3.00 g.) and HGlu(tBu)OMe hydrochloride salt (2.54 g.) by the mixed anhydride method using isobutyl chloroformate gave ZPhe-Glu(tBu)OMe in 88% yield. Debenzyloxycarbonylation of ZPhe-Glu(tBu)OMe (4.30 g.) by hydrogenation with palladium catalyst gave HPhe-Glu(tBu)OMe, which was not isolated but immediately condensed with BocPro-PheOH (3.12 g.) using dicyclohexylcarbodiimide and hydroxysuccinimide, affording BocPro-Phe-Phe-Glu(tBu)OMe in 22% yield. Hydrazinolysis of BocPro-Phe-Phe-Glu(tBu)OMe (1.09 g.) gave BocPro-Phe-Phe-Glu(tBu)NHNH2 in 58% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04472305 |
| Source dataset | uspto-grants-1984_09 |
| ORD ID | ord-a9b9db0a55fe4e48b740bcc8290e5421 |
| Source note | uspto-grants-1984_09 |