HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diphenylphosphinic chloride → BocPro-Phe-PheOMe
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diphenylphosphinic chloride | HCID 73910 | — |
| Reactant | 1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)- | HCID 85083 | — |
| Reactant | HCID 131713766 | HCID 131713766 | — |
| Product | BocPro-Phe-PheOMe | HCID 131713692 | 67% |
Reaction Steps
Condensation of ZPheOH (29.2 g.) and HPheOMe (21.6 g.) by the mixed anhydride method using isobutyl chloroformate gave ZPhe-PHeOMe in 57% yield. Debenzyloxycarbonylation of ZPhe-PHeOMe (26.4 g.) by hydrogenation in acidified methanol with palladium catalyst gave HPhe-PheOMe in 86% yield. Condensation of BocProOH (6.46 g.) and HPhe-PheOMe hydrochloride (10.9 g.) by the mixed anhydride method using diphenylphosphinyl chloride gave BocPro-Phe-PheOMe in 67% yield. Hydrazinolysis of BocPro-Phe-PheOMe (9.57 g.) gave BocPro-Phe-Phe-NHNH2 in 92% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04472305 |
| Source dataset | uspto-grants-1984_09 |
| ORD ID | ord-6ddaf885ad7a4247ab024bb8e621605e |
| Source note | uspto-grants-1984_09 |