HuagongsheHuagongshe Chemistry Print Report · For research reference only
Chlorotrimethylsilane → Methyl L-ornithine dihydrochloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Chlorotrimethylsilane | HCID 6397 | — |
| Reactant | 2-Formylphenylboronic acid | HCID 292189 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | (2S)-5-amino-2-{[(tert-butoxy)carbonyl]amino}pentanoic acid | HCID 7018784 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Triethylamine methanol | HCID 22728368 | — |
| Product | Methyl L-ornithine dihydrochloride | HCID 14273060 | — |
Reaction Steps
Nα-tert-Butyloxycarbonyl-ornitine 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 treatment with methanol and trimethylsilyl chloride, 10:1, to give N′-(2-boronobenzyl), methyl ornitinate, dihydrochloride.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07316999B2 |
| Source dataset | uspto-grants-2008_01 |
| ORD ID | ord-e5be11ac50d145e5aeab1635078a5117 |
| Source note | uspto-grants-2008_01 |