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4-Ethylphenyl isocyanate → 4-(2-Chlorobenzylamino)-3,3-dimethyl-4-oxobutyl 4-ethylphenylcarbamate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 4-Ethylphenyl isocyanate | HCID 90007 | — |
| 反応物 | N-(2-chlorobenzyl)-4-hydroxy-2,2-dimethylbutanamide | HCID 59778491 | — |
| 触媒 | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | 4-(2-Chlorobenzylamino)-3,3-dimethyl-4-oxobutyl 4-ethylphenylcarbamate | HCID 25026416 | 25% |
反応手順
To a solution of N-(2-chlorobenzyl)-4-hydroxy-2,2-dimethylbutanamide (400 mg, 1.6 mmol) in THF (25 mL) were added 4-ethylphenylisocyanate (276 μL, 1.92 mmol, 1.2 equiv.) and DMAP (293 mg, 2.4 mmol, 1.5 equiv.). The reaction mixture was stirred overnight. The reaction mixture was concentrated. The resulting residue was purified on RP-HPLC using a mixture of acetonitrile and H2O, and further purified by flash column chromatography using a mixture of hexanes and EtOAc to give 4-(2-chlorobenzylamino)-3,3-dimethyl-4-oxobutyl 4-ethylphenylcarbamate (160 mg, 25%). LRMS (M+H+) m/z 403.1.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08071625B2 |
| 出典データセット | uspto-grants-2011_12 |
| ORD ID | ord-5a3700b4a789410c9586979b71c72201 |
| 出典メモ | uspto-grants-2011_12 |