化工社化工社 化学情報印刷レポート · 研究参考用
Dicyclohexylcarbodiimide → Acetyl-3-phenylthiopropionate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Dicyclohexylcarbodiimide | HCID 10868 | — |
| 反応物 | Menthone | HCID 26447 | — |
| 反応物 | Boron | HCID 5462311 | — |
| 反応物 | alpha-Methoxy-alpha-trifluoromethylphenylacetic acid, (-)- | HCID 6992788 | — |
| 反応物 | tertbutyl 3(R)-benzoylamino-2(S)-hydroxy-3-phenylthiopropionate | HCID 86752783 | — |
| 触媒 | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 生成物 | Acetyl-3-phenylthiopropionate | HCID 54171142 | — |
反応手順
A pure sample of tertbutyl 3(R)-benzoylamino-2(S)-hydroxy-3-phenylthiopropionate was obtained via the same reaction sequence, but using the boron reagent di{[(1S,2S,5R)-2-isopropyl-5-methylcyclohex-1-yl]-methyl}boron bromide, derived from (-)menthone. Compound tertbutyl 3(R)-benzoylamino-2(S)-hydroxy-3-phenylthiopropionate was treated with excess (S)-(-)-α-methoxy-α-(trifluoromethyl) phenylacetic acid in dichloromethane in the presence of 1,3-dicyclohexylcarbodiimide (DCC) and catalytic 4-dimethylaminopyridine (DMAP). The Mosher derivative tertbutyl 3(R)-benzoylamino-2(S)-O-[(S)-α-methoxy-α-trifluoromethyl)phenyl]acetyl-3-phenylthiopropionate was obtained:
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US05767282 |
| 出典データセット | uspto-grants-1998_06 |
| ORD ID | ord-161ad47b2c054bd398e35e0a3f26f471 |
| 出典メモ | uspto-grants-1998_06 |