HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diphenylphosphinic chloride → BocPro-MePheOMe
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diphenylphosphinic chloride | HCID 73910 | — |
| Reactant | 1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)- | HCID 85083 | — |
| Reactant | methyl (2S)-2-(methylamino)-3-phenylpropanoate | HCID 7021804 | — |
| Product | BocPro-MePheOMe | HCID 131713806 | 77% |
Reaction Steps
Condensation of BocProOH (4.30 g.) and HMePheOMe (2.74 g.) by the mixed anhydride method using diphenylphosphinyl chloride gave BocPro-MePheOMe in 77% yield. Demethylation of BocPro-MePheOMe (3.0 g.) using aqueous sodium hydroxide gave BocPro-MePheOH in 83% yield. Condensation of BocPro-MePheOH (1.71 g.) and HPheOBz (2.14 g.) using dicyclohexylcarbodiimide and N-hydroxysuccinimide gave BocPro-MePhe-PheOBz in 76% yield. Debenzylation of BocPro-MePhe-PheOBz (2.0 g.) by hydrogenation with palladium catalyst gave BocPro-MePhe-PheOH in 100% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04472305 |
| Source dataset | uspto-grants-1984_09 |
| ORD ID | ord-edaf951b211b483ab9b652082d834c45 |
| Source note | uspto-grants-1984_09 |