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4-(Dimethylamino)Benzaldehyde → 2,2-Dimethyl-3alpha-cyano-6alpha-(p-dimethylamino-alpha-hydroxybenzyl)penam
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 4-(Dimethylamino)Benzaldehyde | HCID 7479 | — |
| 反応物 | 2,2-Dimethyl-3alpha-cyano-6alpha-bromopenam | HCID 12944713 | — |
| 触媒 | Zinc | HCID 23994 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 生成物 | 2,2-Dimethyl-3alpha-cyano-6alpha-(p-dimethylamino-alpha-hydroxybenzyl)penam | HCID 70545653 | — |
| 生成物 | 2,2-Dimethyl-3alpha-cyano-6beta-(p-dimethylamino-alpha-hydroxybenzyl)penam | HCID 70546902 | — |
反応手順
A solution of 100 mg 2,2-dimethyl-3α-cyano-6α-bromopenam in 40 ml dry tetrahydrofuran is stirred with 60 mg p-dimethylaminobenzaldehyde and 500 mg zinc for about 12 hours at room temperature. The reaction mixture is then diluted in ethyl acetate, washed with aqueous sodium chloride and dried over anhydrous sodium sulfate. Chromatography of the mixture on silica gel affords, in 11:1 ratio, 2,2-dimethyl-3α-cyano-6α-(p-dimethylamino-α-hydroxybenzyl)penam and 2,2-dimethyl-3α-cyano-6β-(p-dimethylamino-α-hydroxybenzyl)penam. The 6α-compound has the following formula: ##STR39##
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US04283531 |
| 出典データセット | uspto-grants-1981_08 |
| ORD ID | ord-778f6392483544c6bae51ae7e02cf154 |
| 出典メモ | uspto-grants-1981_08 |