HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1877136Generated: October 29, 2026
Ethyl 3-[{[4-({1-[5-(3-methoxyphenyl)-2-methylfuran-3-yl]-3-methylbutyl}amino)phenyl]carbonyl}(methyl)amino]propanoate → 3-[{[4-({1-[5-(3-Methoxyphenyl)-2-methylfuran-3-yl]-3-methylbutyl}amino)phenyl]carbonyl}(methyl)amino]propanoic acid
https://huagongshe.com/reaction/1877136
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl 3-[{[4-({1-[5-(3-methoxyphenyl)-2-methylfuran-3-yl]-3-methylbutyl}amino)phenyl]carbonyl}(methyl)amino]propanoate | HCID 68511355 | — |
| Solvent | Ethanol hexane | HCID 21879635 | — |
| Product | 3-[{[4-({1-[5-(3-Methoxyphenyl)-2-methylfuran-3-yl]-3-methylbutyl}amino)phenyl]carbonyl}(methyl)amino]propanoic acid | HCID 59529401 | 92% |
Reaction Steps
Ethyl 3-[{[4-({1-[5-(3-methoxyphenyl)-2-methylfuran-3-yl]-3-methylbutyl}amino)phenyl]carbonyl}(methyl)amino]propanoate (1200 mg) which is a synthetic intermediate in Example 151 was dissolved in ethanol-hexane (6:4, volume ratio), and the solution was subjected to HPLC using CHIRALPAK AD (50 mmID×500 mL, manufactured by DAICEL CHEMICAL INDUSTRIES, LTD.) and eluted with ethanol-hexane (6:4, volume ratio) as mobile phase at 30° C., a flow rate 60 mL/min. The fractions showing a peak with retention time 11.1 min were collected, and concentrated. The obtained amorphous compound (598 mg) was dissolved in ethanol (5 mL) and tetrahydrofuran (5 mL), lithium hydroxide (2.5 mL) was added, and the mixture was stirred at room temperature for 1 hr. The solvent was evaporated under reduced pressure, and water (20 mL) was added. The mixture was neutralized with 1N hydrochloric acid under ice-cooling, and stirred for 1 hr. The resulting precipitate was collected by filtration and dried to give the title compound (518 mg, 92%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08309580B2 |
|---|
| Source dataset | uspto-grants-2012_11 |
|---|
| ORD ID | ord-efe6c87bae92452b9a2acb7e42744725 |
|---|
| Source note | uspto-grants-2012_11 |
|---|