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Dicyclohexylcarbodiimide → (R)-phenylmethyl-[1-methyl-2-oxo-2-(1H-pyrrol-1-ylamino)ethyl]carbamate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Dicyclohexylcarbodiimide | HCID 10868 | — |
| 反応物 | N-Cbz-d-alanine | HCID 70832 | — |
| 反応物 | 1-Aminopyrrole | HCID 136589 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 生成物 | (R)-phenylmethyl-[1-methyl-2-oxo-2-(1H-pyrrol-1-ylamino)ethyl]carbamate | HCID 131718294 | 90.8% |
反応手順
To a stirred solution consisting of carbobenzyloxy-D-alanine (10.0 g) and N-aminopyrrole (3.68 g) in dry DCM (224 ml) was added DCC (9.71 g) at 0° C. under nitrogen. The cooling bath was removed after ten minutes and the reaction mixture was allowed to stir at room temperature for 24 hours. The suspension was filtered and the DCU filter cake was washed with hot ethyl acetate. Concentration of the filtrate gave the crude product. Recrystallization from EtOAc/hexane afforded 11.69 g of the desired product as a solid, m.p. 172°-174° C.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US05274116 |
| 出典データセット | uspto-grants-1993_12 |
| ORD ID | ord-7d0b79cdba62427f8bfa53befbba185c |
| 出典メモ | uspto-grants-1993_12 |