Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | (R)- 3-Amino-5phenyl-pentanoic acid | HCID 7009759 | — |
| Reactant | Sodium methanolate methanol | HCID 23694274 | — |
| Reactant | Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate | HCID 89812860 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 89812813 | HCID 89812813 | 43% |
Reaction Steps
1-Cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (75 mg, 0.234 mmol) and 3-(R)-Amino-5-phenyl-pentanoic acid (193 mg, 1.0 mmol) were placed in a CEM 10 mL Microwave vessel and sodium methoxide-methanol solution (0.5 M; 2.0 mL, 1.0 mmol) was added via syringe. The vessel was sealed and heated to 130° C. in a CEM microwave apparatus for 4.5 hours. The reaction mixture was diluted with water and treated with 1N hydrochloric acid and extracted three times with ethyl acetate then dried over sodium sulfate. The crude product was purified by MPLC (methylene chloride-methanol) to provide the title compound as an off-white solid in 43% yield. MS ESI(−) m/e: 480.1305 (M−1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09409892B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-1939de1f1ff845099fa057dba18857ab |
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| Source note | uspto-grants-2016_08 |
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