関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | 1-Hydroxybenzotriazole | HCID 75771 | — |
| 反応物 | Diisopropylethylamine | HCID 81531 | — |
| 反応物 | Ethyl N-methylaminoacetate hydrochloride | HCID 171173 | — |
| 反応物 | (2R)-1-((Benzyloxy)carbonyl)piperidine-2-carboxylic acid | HCID 688346 | — |
| 反応物 | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 生成物 | Cbz-D-hPro-N(Me)Gly-OEt | HCID 15481639 | 80.1% |
反応手順
To a stirring solution of Cbz-D-hPro-OH (6.0 g, 22.8 mmol), sarcosine ethyl ester hydrochloride (4.38 g, 28.5 mmol), 1-hydroxybenzotriazole (3.08 g, 22.8 mmol), and N,N-diisopropylethylamine (11.9 mL, 68.4 mmol) in dichloromethane (200 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (5.46 g, 28.5 mmol). After stirring for 12 hours, the solvent was removed in vacuo and the residue was dissolved in ethyl acetate (500 mL), washed twice with 1N citric acid (200 mL), twice with saturated aqueous NaHCO3, and twice with a saturated aqueous sodium chloride solution. The organic phase was then dried with MgSO4, filtered, and concentrated in vacuo. The residue was chromatographed over silica gel, eluting with a step gradient of hexanes through 50% ethyl acetate/hexanes. Fractions containing product (based on TLC) were combined and concentrated to give 6.62 g (80%) of a colorless oil.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 特許番号 | US05885967 |
|---|
| 出典データセット | uspto-grants-1999_03 |
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| ORD ID | ord-14502c810e894b69843cdd3e6730ba19 |
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| 出典メモ | uspto-grants-1999_03 |
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