HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-(Dimethylamino)-1,2-propanediol → (2,3-Bis-octadec-9-enyloxypropyl)-(8-hydroxy-3,6-dioxooctyloxycarbonylbutyl)-dimethylammonium bromide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-(Dimethylamino)-1,2-propanediol | HCID 79078 | — |
| Reactant | 9-Octadecen-1-ol, methanesulfonate, (9Z)- | HCID 118861 | — |
| Reactant | 1-Propanamine, N,N-dimethyl-2,3-bis[(9Z)-9-octadecenyloxy]- | HCID 53844259 | — |
| Reactant | 5-Bromopentanoic acid 8-hydroxy-3,6-dioxooctyl ester | HCID 86643550 | — |
| Solvent | Acetone | HCID 180 | — |
| Product | (2,3-Bis-octadec-9-enyloxypropyl)-(8-hydroxy-3,6-dioxooctyloxycarbonylbutyl)-dimethylammonium bromide | HCID 86643548 | 27% |
Reaction Steps
A mixture of (2,3-bis-octadec-9-enyloxypropyl)-dimethylamine 4 (378 mg, 0.61 mmol) (synthesised from octadec-9-enyl mesylate and 3-dimethylamino-1,2-propanediol as described previously by Hurley et al., J. Org. Chem., 2004, 69, 980-984) and 3 (335 mg, 1.07 mmol) in acetone (5 ml) was stirred in a sealed-tube at 80° C. for 48 h. After cooling, the solvent was evaporated in vacuo. Purification by flash chromatography on silica (gradient; 5% to 10% methanol in dichloromethane) gave ME42 as an orange oil (140 mg, 27%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09399016B2 |
| Source dataset | uspto-grants-2016_07 |
| ORD ID | ord-5f67299e3cc9467f89fa2a7044a78088 |
| Source note | uspto-grants-2016_07 |