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(R)-1-Phenylpropylamine → (R)-1-(benzyloxycarbonylamino)-2-methylpropylphosphonous acid
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | (R)-1-Phenylpropylamine | HCID 5324978 | — |
| 反応物 | 1-Carbobenzyloxyamino-2-methylpropanephosphonous acid | HCID 21325852 | — |
| 溶媒 | Ethanol | HCID 702 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 生成物 | (R)-1-(benzyloxycarbonylamino)-2-methylpropylphosphonous acid | HCID 67375324 | 32.4% |
反応手順
A solution of 1-(benzyloxycarbonylamino)-2-methylpropylphosphonous acid (3.4 g, 12.5 mmol) in 20 mL of absolute ethanol was heated to reflux and (R)-(+)-methylbenzylamine (96% ee, 1.5 g, 12.5 mmol) was added. The resulting mixture was diluted with 120 mL of ethyl acetate. The precipitate was filtered off, washed with 100 mL of ethyl acetate and 100 mL of ether, dried in vacuo to afford (R)-1-(benzyloxycarbonylamino)-2-methylpropylphosphonous acid as a white solid (1.1 g) with a rotation [α]D=−10.87° (c=10 mg/mL 9:1 DMF-H2O). This material was found to be 93% ee by chiral HPLC.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08008325B2 |
| 出典データセット | uspto-grants-2011_08 |
| ORD ID | ord-6ea9d939b9b74e04a2d660d2ee438185 |
| 出典メモ | uspto-grants-2011_08 |