HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → Tri-Boc Lysine-beta-aminoethyl Ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | Propanoic acid, 3-amino-2-hydroxy-, 1,1-dimethylethyl ester | HCID 22707757 | — |
| Reactant | Di-tert-butoxycarbonyl-lysine | HCID 22792075 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Tri-Boc Lysine-beta-aminoethyl Ester | HCID 131730895 | 68% |
Reaction Steps
Di-Boc lysine (770 grams, 2.2 mol) was dissolved in dichloromethane (4 liters). Bocethanolamine (340 grams, 2.1 mol) was added to the solution, along with 4-dimethylaminopyridine (50 grams.) EDC-HCl (450 grams, 2.35 mol) was added and the mixture was allowed to stir overnight at room temperature. Water (2 liters) was added and the mixture was stirred for 30 minutes. The layers were separated, and the aqueous layer was extracted with dichloromethane. The combined organics were washed with saturated sodium bicarbonate, 1N HCl solution, and brine. Solvent was removed under reduced pressure to give an oil. Mass recovery was 770 grams (68% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08552217B2 |
| Source dataset | uspto-grants-2013_10 |
| ORD ID | ord-02a25817089144c5a5880e63fe2b155b |
| Source note | uspto-grants-2013_10 |