HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Hydroxybenzotriazole → N-(3,3-diethoxy-propyl)-3-methoxy-2-methoxymethyl-2-methyl-propionamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1-Amino-3,3-diethoxypropane | HCID 521029 | — |
| Reactant | 3-Methoxy-2-(methoxymethyl)-2-methylpropanoic acid | HCID 21911931 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | N-(3,3-diethoxy-propyl)-3-methoxy-2-methoxymethyl-2-methyl-propionamide | HCID 86641927 | 80.7% |
Reaction Steps
5 g of 3-methoxy-2-methoxymethyl-2-methyl-propionic acid (prepared as described in EP609058) were dissolved in 49 mL of DCM and 12 mL of THF. 11.4 mL of DIPEA, 5.84 g of HOBt, 7.07 g of EDC and 5.45 g of 3,3-diethoxy-propylamine were added sequentially. The mixture was stirred for 23 h at rt, diluted with DCM and washed with sat. NaHCO3. The organic phase was dried over anh. Na2SO4 and concentrated in vacuo. The resulting crude material was purified by CC using Hept/EtOAc from 3/1 to 0/1 as eluant to yield 7.25 g of N-(3,3-diethoxy-propyl)-3-methoxy-2-methoxymethyl-2-methyl-propionamide as a yellowish oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08436205B2 |
| Source dataset | uspto-grants-2013_05 |
| ORD ID | ord-e3183eda780f473aa91094352e5fc363 |
| Source note | uspto-grants-2013_05 |