HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl iodide → (2S)-2-{[(tert-butoxy)carbonyl](methyl)amino}-4-methylpentanoic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | L-Leucine, N-((1,1-dimethylethoxy)carbonyl)- | HCID 83170 | — |
| Product | (2S)-2-{[(tert-butoxy)carbonyl](methyl)amino}-4-methylpentanoic acid | HCID 7010555 | 73% |
Reaction Steps
Methylation of BocLeuOH (12.5 g.) using sodium hydride and methyl iodide gave BocMeLeuOH in 73% yield. Condensation of BocMeLeuOH (3.7 g.) and HMetNH2 hydrochloride salt (2.8 g.) by the mixed anhydride method using isobutyl chloroformate gave BocMeLeu-MetNH2 in 56% yield. De-t-butoxycarbonylation of BocMeLeu-MetNH2 (3.3 g.) using hydrogen chloride in ethyl acetate gave MeLeu-MetNH2 in 64% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04472305 |
| Source dataset | uspto-grants-1984_09 |
| ORD ID | ord-0524d95f27054a3d9c9a20c3974753d3 |
| Source note | uspto-grants-1984_09 |