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Penicillin G → 4-methoxybenzyl (2RS)-2-hydroxy-2-[(3R,4R)-4-mercapto-3-phenylacetamidoazetidin-2-on-1-yl]acetate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Penicillin G | HCID 5904 | — |
| 反応物 | p-Toluenesulfonic acid | HCID 6101 | — |
| 反応物 | Penicillin V | HCID 6869 | — |
| 反応物 | 4-Methoxybenzyl (RS)-2-hydroxy-2-[(lR,5R)-3-benzyl-4-thia-2,6-diazabicyclo[3.2.0)hept-2-en-7-on-6-yl]acetate | HCID 53656123 | — |
| 溶媒 | Acetone | HCID 180 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 生成物 | 4-methoxybenzyl (2RS)-2-hydroxy-2-[(3R,4R)-4-mercapto-3-phenylacetamidoazetidin-2-on-1-yl]acetate | HCID 54454956 | — |
反応手順
Toluene-4-sulphonic acid (6.0g, 31.5mmol) in water (15ml) was added to a solution of 4-methoxybenzyl (2RS)-2-hydroxy-2-[(1R,5R)-3-benzyl-4-thia-2,6-diazabicyclo [3.2.0]hept-2-en-7-on-6-yl]acetate (7.42g, 18.0mmol) prepared from Penicillin G as described for the benzhydryl ester derived from Penicillin V, S. Yamamoto, N. Haga, T. Aoki, S. Hayashi, H. Tanida, and W. Nagata, Heterocycles, 1977, 8, 283) in dichloromethane (30ml) and acetone (30ml) . After stirring for 2.5 h at room temperature, the reaction mixture was diluted with dichloromethane, washed with water (x2), dried and concentrated in vacuo to yield crude 4-methoxybenzyl (2RS)-2-hydroxy-2-[(3R,4R)-4-mercapto-3-phenylacetamidoazetidin-2-on-1-yl]acetate as a yellow foam.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US06020329 |
| 出典データセット | uspto-grants-2000_02 |
| ORD ID | ord-42441a00ee534f25b7bdac242c274c7b |
| 出典メモ | uspto-grants-2000_02 |