化工社化工社 化学情報印刷レポート · 研究参考用
Sodium Carbonate → (2S)-1-(4-methylbenzenesulfonyl)pyrrolidine-2-carboxylic acid
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Sodium Carbonate | HCID 10340 | — |
| 反応物 | 4-(Chlorosulfonyl)benzoic acid | HCID 82385 | — |
| 反応物 | methyl L-prolinate hydrochloride | HCID 2733200 | — |
| 反応物 | Pentafluorophenyl Trifluoroacetate | HCID 4327891 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Pyridine | HCID 1049 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 溶媒 | Triethylamine | HCID 8471 | — |
| 生成物 | (2S)-1-(4-methylbenzenesulfonyl)pyrrolidine-2-carboxylic acid | HCID 691957 | — |
反応手順
N-tosyl-proline derivatives were synthesized as follows. Proline methyl ester hydrochloride was reacted with 4-(chlorosulfonyl)benzoic acid and sodium carbonate in water. The product was converted to the pentafluorophenyl ester by reacting it with pentafluorophenyl trifluoroacetate and pyridine in N,N-dimethylformamide, and purified via flash chromatography. This activated ester was then reacted with the methyl-ester of glutamate (or any of the other amino acids tested) in the presence of triethylamine and dichloromethane, the product purified by flash chromatography, and the methyl esters hydrolyzed with lithium hydroxide in water. The final products were purified via reverse-phase HPLC and lyophilized.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US06998233B2 |
| 出典データセット | uspto-grants-2006_02 |
| ORD ID | ord-9f53c9452f294edf8695ae1906d4800c |
| 出典メモ | uspto-grants-2006_02 |