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Triethylamine → N-methyl-N-hydroxy-4-(3-(2-benzyloxyphenyl)propyl)benzamide
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Triethylamine | HCID 8471 | — |
| 反応物 | Dicyclohexylcarbodiimide | HCID 10868 | — |
| 反応物 | N-methylhydroxylamine hydrochloride | HCID 77906 | — |
| 反応物 | 4-(3-(2-Benzyloxyphenyl)propyl]benzoic acid | HCID 18973764 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 生成物 | N-methyl-N-hydroxy-4-(3-(2-benzyloxyphenyl)propyl)benzamide | HCID 18973882 | 36.1% |
反応手順
A mixture of 4-(3-(2-benzyloxyphenyl)propyl]benzoic acid (1.0 g), 1-HOBT (0.39 g) and DCCI (0.595 g) in DMF (10 ml) was stirred for 3 hours, then added to a solution of N-methylhydroxylamine HCl (0.24 g) and Et3N (0.29 g) in CH2Cl2 (10 ml) and stirred for 70 hours. The product was extracted in 2N aqueous KOH and washed with ethyl acetate. The aqueous solution was acidified with concentrated HCl and extracted with diethyl ether. The solvent was evaporated and the residue subjected to flash chromatography on silica gel (using diethyl ether:methanol (95:5) as eluant) to give N-methyl-N-hydroxy-4-(3-(2-benzyloxyphenyl)propyl)benzamide as a gum (0.39 g).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US05811459 |
| 出典データセット | uspto-grants-1998_09 |
| ORD ID | ord-5bfdfe74464e4b01b0b7df5c5b5d7ece |
| 出典メモ | uspto-grants-1998_09 |