HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ammonium Chloride → 2-(4-Adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Reactant | 2-(4-Adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid | HCID 24966534 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-(4-Adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid amide | HCID 24966896 | 4% |
Reaction Steps
To solution of 2-(4-adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid (72.1 mg, 0.18 mmol), ammonium chloride (19.1 mg, 0.36 mmol) in DMF 4.0 mL was added HBTU (136.53 mg, 0.36 mmol) and DIPEA (0.063 ml, 0.36 mmol). After stirring at room temperature, the mixture was partitioned between ethyl acetate and brine. The organic phase was dried (MgSO4 anh), and concentrated. The residue was purified by silica gel column chromatography (CH2Cl2:MeOH=15:1) to give 2-(4-adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid amide as a yellow solid (2.7 mg, 4% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08394799B2 |
| Source dataset | uspto-grants-2013_03 |
| ORD ID | ord-961e7442b765492fb8d789a3cc642d17 |
| Source note | uspto-grants-2013_03 |