HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diphenylphosphinic chloride → BocPro-MeDTrpOMe
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diphenylphosphinic chloride | HCID 73910 | — |
| Reactant | 1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)- | HCID 85083 | — |
| Reactant | N-Methyl-D-tryptophan Methyl Ester | HCID 12787320 | — |
| Product | BocPro-MeDTrpOMe | HCID 131713818 | 69% |
Reaction Steps
Condensation of BocProOH (4.63 g.) and MeDTrpOMe (5.00 g.) by the mixed anhydride method using diphenylphosphinyl chloride gave BocPro-MeDTrpOMe in 69% yield. Demethylation of BocPro-MeDTrpOMe (6.33 g.) using aqueous sodium hydroxide gave BocPro-MeDTrpOH in 77% yield. Condensation of BocPro-MeDTrpOH (3.60 g.) and HPheOBz (3.70 g.) using dicyclohexylcarbodiimide and N-hydroxysuccinimide gave BocPro-MeDTrp-PheOBz in 83% yield. Debenzylation of BocPro-MeDTrp-PheOBz (4.60 g.) by hydrogenation with palladium catalyst gave BocPro-MeDTrp-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-fad56c59c9714e7fb25a3d39e4862a23 |
| Source note | uspto-grants-1984_09 |