Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanolamine | HCID 700 | — |
| Reactant | 1,1'-Carbonyldiimidazole | HCID 68263 | — |
| Reactant | HCID 60029928 | HCID 60029928 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 69735253 | HCID 69735253 | 81.2% |
Reaction Steps
A mixture of 1,1′-carbonyldiimidazole (49 mg, 0.30 mmol, 0.60M in DMF) and 3-{[(2-{[(1S)-2-(1H-imidazol-1-yl)-1-phenylethyl]oxy}-5-oxo-5,6,7,8-tetrahydro-1-naphthalenyl)methyl]sulfanyl}benzoic acid (50 mg, 0.10 mmol, 0.20M in DMF) in a capped vial were placed in a heater-shaker at 55° C. for 20 min. It was removed from the heater-shaker and stood at room temperature. A solution of 2-aminoethanol (31 mg, 0.50 mmol, 1.0M in DMF) was added and the reaction mixture was further shaken at room temperature over-night. Water (6 ml) was added and the mixture was shaken at room temperature for 10 min. before being stored in refrigerator over-night. The precipitate was filtered, washed with cold water (2×0.5 ml) and dried in a vacuum oven at 40° C. until constant weight was obtained. 44 mg of the required benzamide was obtained as a beige solid: Low resolution mass spectrum (LC-MS, APCI) m/z 542 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06943183B2 |
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| Source dataset | uspto-grants-2005_09 |
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| ORD ID | ord-732c5ec67eed4baebbbdb9d9c33a1408 |
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| Source note | uspto-grants-2005_09 |
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