HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzaldehyde → Methyl L-lysinate dihydrochloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzaldehyde | HCID 240 | — |
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | Chlorotrimethylsilane | HCID 6397 | — |
| Reactant | 687-64-9 | HCID 117779 | — |
| Reactant | Trimethylsilyldiazomethane | HCID 167693 | — |
| Reactant | epsilon-tert-Butyloxycarbonyl-lysine | HCID 2733284 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | Sodium | HCID 5360545 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | Methyl L-lysinate dihydrochloride | HCID 117778 | — |
Reaction Steps
Nα-tert-Butyloxycarbonyl-lysine was reacted with trimethylsilyldiazomethan in ethanol. The resulting methyl ester amine was transformed to the Nε-methyl derivative via benzaldehyde and sodium borohydride, formaldehyde and sodium boronhydride and hydrogenolysis (Andruszkiewicz, J. Pol. Chem. 1988, 62, 257) followed by N-alkylation with 2-(pinacolborono)benzyl bromide. The resulting Nα-tert-butyloxycarbonyl, Nε-methyl, Nε-(2-pinacolboronobenzyl) methyl lysinate was treated with methanol and trimethylsilyl chloride, 10:1, to give Nε-methyl, 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-e54f311abcd944dcab3e5f668b1209c7 |
| Source note | uspto-grants-2008_01 |