HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → Leucyl-phenylalanine amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | tert-butyl N-[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate | HCID 7385739 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | Leucyl-phenylalanine amide | HCID 3082491 | 74% |
Reaction Steps
De-(1,1-dimethylethoxy)carbonylation of Boc-Leu-Phe-NH2 (24.0 g.) was carried out using hydrogen chloride in ethyl acetate (4.4N, 200 ml.) for 2 hr. at room temperature. Upon attempted extraction with ethyl acetate the product unexpectedly entered the saturated aqueous sodium bicarbonate wash solution, which was subjected in its entirety to reverse phase HPLC on octadecylsilated silica gel. The column was washed with water. The product was eluted with methanol and crystallized from ethanol-ether-hexane affording H-Leu-Phe-NH2 as a tan solid (13.0 g., 74% yield, m.r. 127°-131° C.).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05378803 |
| Source dataset | uspto-grants-1995_01 |
| ORD ID | ord-98a9155ea31a457a98cd3c88e1ce2607 |
| Source note | uspto-grants-1995_01 |