HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → Ethyl (2R)-2-(6-chloro-1H-benzimidazole-2-yl)-2-hydroxy-3-phenylpropanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 4-Chloro-1,2-diaminobenzene | HCID 7263 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | (2R)-2-benzyl-3-ethoxy-2-hydroxy-3-oxopropanoic acid | HCID 71727620 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | Ethyl (2R)-2-(6-chloro-1H-benzimidazole-2-yl)-2-hydroxy-3-phenylpropanoate | HCID 90395277 | — |
Reaction Steps
To a mixture of (2R)-2-benzyl-3-ethoxy-2-hydroxy-3-oxopropanoic acid (320 mg), HATU (562 mg), 3,4-diamino-chlorobenzene (230 gm) was added 4 mL of DMF at rt. The mixture was stirred at rt overnight. To this mixture was added water and ethyl acetate. The organic layer was washed with water and then concentrated in vacuo after being dried with mangesium sulfate. The residue, without purification, was dissolved in 3 mL of acetic acid and heated at 75 degrees for 2 h. The mixture was then concentrated and purified by Biotage silica gel column chromatography (8-35% ethyl acetate in hexanes) to give the title product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09193717B2 |
| Source dataset | uspto-grants-2015_11 |
| ORD ID | ord-18194b9a56fd4636a005a5fff3cd142c |
| Source note | uspto-grants-2015_11 |