Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Isopropyl chloroformate | HCID 7917 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | HCID 178525557 | HCID 178525557 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 178513915 | HCID 178513915 | 100.1% |
Reaction Steps
Trans-[4-(4-{3-[(2-phenyl-5-trifluoromethyloxazole-4-carbonyl)amino]propionylamino}phenyl)cyclohexyl]acetic acid (41 mg, 0.07 mmol) was added to DCM (4 mL) and DMF (1 mL) solution. Isopropyl chloroformate (0.02 mL, 0.11 mmol) and triethyl amine (0.2 mL, 0.15 mmol) were added dropwise thereto at 0° C., a temperature of the product was raised to room temperature, and stirred for 2 hours. Then, 0.5 M ammonia dissolved in 1,4-dioxane was added and stirred for 2 hours. Ethyl acetate (20 mL) and water (40 mL) were added to the reaction mixture. Then, the organic layer was separated and the product was dried with anhydrous sodium sulfate to prepare a solid under reduced pressure. The product was purified by chromatography using methanol/DCM 2-10% to obtain the desired compound (38 mg, 93%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09321728B2 |
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| Source dataset | uspto-grants-2016_04 |
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| ORD ID | ord-16254e996d6f462192efc285c952032c |
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| Source note | uspto-grants-2016_04 |
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