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Ethanol → (2R,4R)-5-(3'-Chlorobiphenyl-4-yl)-2-hydroxy-4-{[5-(4-methoxybenzyloxy)-1-methyl-1H-pyrazole-3-carbonyl]amino}pentanoic Acid
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Ethanol | HCID 702 | — |
| 反応物 | Water | HCID 962 | — |
| 反応物 | Lithium Hydroxide | HCID 3939 | — |
| 反応物 | Dimethylformamide | HCID 6228 | — |
| 反応物 | Diisopropylethylamine | HCID 81531 | — |
| 反応物 | O-(6-Chlorobenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate | HCID 42624899 | — |
| 反応物 | (2R,4R)-4-amino-5-(3'-chlorobiphenyl-4-yl)-2-hydroxypentanoic acid ethyl ester | HCID 86682253 | — |
| 反応物 | 5-(4-Methoxybenzyloxy)-1-methyl-1H-pyrazole-3-carboxylic Acid | HCID 86705138 | — |
| 生成物 | (2R,4R)-5-(3'-Chlorobiphenyl-4-yl)-2-hydroxy-4-{[5-(4-methoxybenzyloxy)-1-methyl-1H-pyrazole-3-carbonyl]amino}pentanoic Acid | HCID 86705139 | 70.5% |
反応手順
5-(4-Methoxy-benzyloxy)-1-methyl-1H-pyrazole-3-carboxylic acid (118.8 mg, 453 mol) was combined with HCTU (187.3 mg, 453 μmol) and DMF (2.0 mL, 25.9 mmol). The mixture was stirred at room temperature for 15 minutes. DIPEA (225 μL, 1.3 mmol) and (2R,4R)-4-amino-5-(3′-chlorobiphenyl-4-yl)-2-hydroxypentanoic acid ethyl ester (150 mg, 430 μmol) were added and the mixture was stirred at room temperature for 15 minutes. The solvent was removed in vacuo. EtOH (1.5 mL, 25.9 mmol) was added, followed by a solution of 1 M LiOH in water (4.3 mL, 4.3 mmol). The mixture was stirred at room temperature for 1 hour. The solvent was removed in vacuo and the product was purified by reverse phase chromatography to yield the title compound (171 mg).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US09108934B2 |
| 出典データセット | uspto-grants-2015_08 |
| ORD ID | ord-7ebbacd29781469a942d8344b2262580 |
| 出典メモ | uspto-grants-2015_08 |