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 | HCID 178445732 | HCID 178445732 | — |
| 生成物 | HCID 178445755 | HCID 178445755 | — |
反応手順
The mixture of (R)-4-(6-(cis-4-butylcyclohexyloxy)naphthalen-2-yl)-4-methyloxazolidin-2-one (294.3 mg, 0.7714 mmol) and lithium hydroxide (203 mg, 8.48 mmol) in Ethanol (4.9 mL, 0.084 mol) and water (1.6 mL, 9.1 mmol) was heated to reflux for overnight. LCMS showed reaction completed. The solvent was removed under vacuum and the residue was partitioned between water and CH2Cl2. The aqueous was extensively extracted with CH2Cl2. And the combined organic phase was dried over Na2SO4. The concentrated residue was taken up into CH2Cl2 and subjected to chromatography purification with CH2Cl2/MeOH (10:90 to 80:20) to give the product. LCMS 339.53 ([M-NH2]+, 100%). 1H NMR (400 MHz, CD3OD) δ ppm 0.92 (t, J=7.0 Hz, 3H), 1.21-1.50 (m, 9H), 1.54 (s, 3H), 1.56-1.71 (m, 4H), 2.05 (brd, J=13.3 Hz, 2 H), 3.71 (AB, J=10.8 Hz, 2H), 4.69 (brs, 1H), 7.14 (dd, J=8.8, 3.3 Hz, 1H), 7.19 (s, 1H), 7.53 (d, J=8.7 Hz, 1H), 7.72 (d, J=8.7 Hz, 1H), 7.76 (d, J=8.7 Hz, 1H), 7.83 (s, 1H).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 特許番号 | US08269043B2 |
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| 出典データセット | uspto-grants-2012_09 |
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| ORD ID | ord-c6310af9961946829e667fbd0a6fcce3 |
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| 出典メモ | uspto-grants-2012_09 |
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