HuagongsheHuagongshe Chemistry Print Report · For research reference only
Chlorotrimethylsilane → Methyl L-lysinate dihydrochloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Chlorotrimethylsilane | HCID 6397 | — |
| Reactant | 2-Formylphenylboronic acid | HCID 292189 | — |
| Reactant | epsilon-tert-Butyloxycarbonyl-lysine | HCID 2733284 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Triethylamine methanol | HCID 22728368 | — |
| Product | Methyl L-lysinate dihydrochloride | HCID 117778 | — |
Reaction Steps
Nα-tert-Butyloxycarbonyl-lysine was reacted with 2-formylphenylboronic acid in methanol-triethylamine and subsequently treated with sodium borohydride (Wiskur et al, Org. Letters 2001, 3, 1311). The resulting secondary amine was transformed to the methyl ester by treament with methanol and trimethylsilyl chloride, 10:1, to give Nε-(2-boronobenzyl), methyl lysinate, dihydrochloride.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07316999B2 |
| Source dataset | uspto-grants-2008_01 |
| ORD ID | ord-c3dfc82ad86c44eea84e45ada6332616 |
| Source note | uspto-grants-2008_01 |