HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-(Boc-amino)-L-alanine → ZPhe-LDap(Boc)OH
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-(Boc-amino)-L-alanine | HCID 10352859 | — |
| Reactant | N-Carbobenzyloxy-L-phenylalanyl N-hydroxysuccinimide ester | HCID 12876457 | — |
| Product | ZPhe-LDap(Boc)OH | HCID 131713742 | 64% |
Reaction Steps
Condensation of ZPheOSu (6.96 g.) and HLDap(Boc)OH (6.0 g.) by the salt coupling method gave ZPhe-LDap(Boc)OH in 64% yield. Condensation of ZPhe-LDap(Boc)OH (4.85 g.) and HLeuOMe (2.73 g.) by the mixed anhydride method using diphenylphosphinic chloride gave ZPhe-LDap(Boc)-LeuOMe in 69% yield. Debenzyloxycarbonylation of ZPhe-LDap(Boc)-LeuOMe (4.15 g.) by hydrogenation with palladium catalyst gave HPhe-LDap(Boc)-LeuOMe in 100% yield. Condensation of BocPro-PheOH (1.09 g.) and HPhe-LDap(Boc)-LeuOMe (1.44 g.) using dicyclohexylcarbodiimide and N-hydroxynorbornenedicarboximide gave BocPro-Phe-Phe-LDap(Boc)-LeuOMe in 75% yield. Hydrazinolysis of BocPro-Phe-Phe-LDap(Boc)-LeuOMe (1.69 g.) gave BocPro-Phe-Phe-LDap(Boc)- LeuNHNH2 in 36% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04472305 |
| Source dataset | uspto-grants-1984_09 |
| ORD ID | ord-076e0beeab714d83b37ab1d58fb33cc2 |
| Source note | uspto-grants-1984_09 |