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Dicyclohexylcarbodiimide → HCID 59401188、化合物
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Dicyclohexylcarbodiimide | HCID 10868 | — |
| 反応物 | 1-Hydroxybenzotriazole | HCID 75771 | — |
| 反応物 | L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]- | HCID 77857 | — |
| 反応物 | 3-Quinuclidinol, (-)- | HCID 91404 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | HCID 59401188 | HCID 59401188 | 80% |
反応手順
To a solution of (S)-2-(tert-butoxycarbonylamino)-3-phenylpropanoic acid (1.03 g, 3.81 mmol) in THF (70 mL), are added DCC (1.03 g, 4.91 mmol), HOBt (660 mg, 4.90 mmol) and 3(R)-quinuclidinol (1.18 g, 9.48 mmol) and the resulting mixture is stirred for 12 hours at RT under nitrogen flowstream (LC-MS monitoring: complete conversion). The solvent is evaporated and the residue is partitioned between EtOAc (100 mL) and 2M K2CO3 (50 mL); the organic layer is separated, washed with brine and dried over Na2SO4. The resulting crude is purified by flash chromatography (DCM/MeOH=95/5, 0.1% NH3 (aq.)) to obtain 1.12 g of I19 (80% yield).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08835682B2 |
| 出典データセット | uspto-grants-2014_09 |
| ORD ID | ord-0857f016133b479ea8a06b8bbeb5fae3 |
| 出典メモ | uspto-grants-2014_09 |