HuagongsheHuagongshe Chemistry Print Report · For research reference only
N-succinimidyl bromoacetate → 2-(1-(2-hydroxyethyl)-2,6-dioxopiperidin-3-yl)isoindolin-1,3-dione (S)-2-(2-bromoacetamido)-3-methylbutanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | N-succinimidyl bromoacetate | HCID 3565210 | — |
| Reactant | 2-(1-(2-hydroxyethyl)-2,6-dioxopiperidin-3-yl)isoindolin-1,3-dione (S)-2-amino-3-methylbutanoate | HCID 71082754 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-(1-(2-hydroxyethyl)-2,6-dioxopiperidin-3-yl)isoindolin-1,3-dione (S)-2-(2-bromoacetamido)-3-methylbutanoate | HCID 86618751 | 56.1% |
Reaction Steps
2-(1-(2-hydroxyethyl)-2,6-dioxopiperidin-3-yl)isoindolin-1,3-dione (S)-2-amino-3-methylbutanoate (1.8 g) was dissolved in DCM (20 mL). 2,5-Dioxopyrrolidinyl bromoacetate (1.04 g) was added to the mixture. The mixture was stirred with a magnetic stirrer at room temperature, and reacted overnight. The solvent was stripped in vacuo. White solid (1.3 g) was obtained after purification of the crude product on silica gel column (eluted with acetic ether:petroleum ether=1:1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08637545B2 |
| Source dataset | uspto-grants-2014_01 |
| ORD ID | ord-37d55e7b07fe47bb92e5ea93f628599f |
| Source note | uspto-grants-2014_01 |