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Diisopropylethylamine → (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(5-chlorothiophene-2-carboxamido)propanoate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Diisopropylethylamine | HCID 81531 | — |
| 反応物 | 5-Chloro-2-thiophenecarboxylic acid | HCID 95048 | — |
| 反応物 | O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733286 | — |
| 反応物 | Methyl 3-amino-N-(tert-butoxycarbonyl)-L-alaninate--hydrogen chloride (1/1) | HCID 71607207 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 生成物 | (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(5-chlorothiophene-2-carboxamido)propanoate | HCID 67155290 | — |
反応手順
5-Chloro-thiophene-2-carboxylic acid (16.26 g, 0.1 mol) in 500 ml DCM was stirred with DIPEA (51.04 ml, 0.3 mol) and TOTU (32.8 g, 0.1 mmol) at RT for 5 min. Commercially available (S)-3-amino-2-tert-butoxycarbonylamino-propionic acid methyl ester hydrochloride (25.4 g, 0.1 mol) were added and the reaction mixture was stirred at RT overnight and then evaporated. The resulting solid was suspended in 400 ml DCM and washed subsequently with sat. aq NaHCO3, 1N HCl and brine. The organic layer was dried with MgSO4, filtered and evaporated. The crude material was triturated with DCM and the solid filtered off. One obtained 18.4 g white, amorphous solid which was used in the next step without further purification.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08378092B2 |
| 出典データセット | uspto-grants-2013_02 |
| ORD ID | ord-76076d44f4b14dc4935e4b6717755c48 |
| 出典メモ | uspto-grants-2013_02 |