HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetonitrile → 4-[3-[6-(3-Bromo-5-dimethylaminomethyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 4-[3-[6-(3-Bromo-5-methanesulfonyloxymethyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester | HCID 59496829 | — |
| Solvent | Dimethylamine | HCID 674 | — |
| Product | 4-[3-[6-(3-Bromo-5-dimethylaminomethyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester | HCID 59496792 | 64% |
Reaction Steps
The a solution of 4-[3-[6-(3-Bromo-5-methanesulfonyloxymethyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (2.5 g, 3.72 mmol) in MeCN (40 mL), N,N-dimethylamine 2M/THF (3.72 mL, 7.44 mmol) was added, and stirred at room temperature overnight. The solvent was removed under reduced pressure. Flash column chromatography (50% EtOAc/Hex) provided a light yellow oil (1.47 g, 64% yield). 1H NMR (CDCl3): δ 7.08 (t, 1H), 7.03 (s, 1H), 6.93 (s, 1H), 6.79 (s, 1H), 6.77 (d, 1H), 6.68 (d, 1H), 4.17-4.06 (m, 4H), 3.99 (dd, 2H), 3.92 (dd, 2H), 3.34 (s, 2H), 2.97 (dd, 2H), 2.63 (dd, 2H), 2.56-2.46 (m, 4H), 2.23 (s, 6H), 2.17-0.89 (m, 16H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08088936B2 |
| Source dataset | uspto-grants-2012_01 |
| ORD ID | ord-c2037e0a609d405c8bde0050d4141745 |
| Source note | uspto-grants-2012_01 |