HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → HCID 71548047, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Palmitoyl chloride | HCID 8206 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | (6S)-N-Benzyl-6-(4-hydroxybenzyl)-8-(naphthalen-1-ylmethyl)-4,7-dioxohexahydro-2H-pyrazino[1,2-a]pyrimidine-1(6H)-carboxamide | HCID 11295786 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 71548047 | HCID 71548047 | 68% |
Reaction Steps
To a solution of (6S)—N-benzyl-6-(4-hydroxybenzyl)-8-(naphthalen-1-ylmethyl)-4,7-dioxooctahydro-1H-pyrazino[1,2-a]pyrimidine-1-carboxamide 60 mg (0.106 mmol) in dry-THF (2 ml), palmitoyl chloride 97 μl (0.319 mmol) and then triethylamine 45 μl (0.319 mmol) were added and stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate (10 ml) and washed with water (10 ml), saturated sodium bicarbonate (10 ml), water (10 ml), and brine (10 ml). The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by Büchi silica gel column chromatography (chloroform:methanol=99:1 to 98:2) to obtain title compound 57.7 mg (68%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09371330B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-cb9a8dfb75e544fc99474ab525818190 |
| Source note | uspto-grants-2016_06 |