4-(Dimethylamino)Benzaldehyde → 2,2-Dimethyl-3alpha-cyano-6alpha-(p-dimethylamino-alpha-hydroxybenzyl)penam

HRID 1680128

反応式

HRID 1680128 の反応式
[CH3:1][C:2]1([CH3:13])[C@H:6]([C:7]#[N:8])[N:5]2[C:9](=[O:12])[C@H:10](Br)[C@H:4]2[S:3]1.[CH3:14][N:15]([CH3:24])[C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=1>O1CCCC1.C(OCC)(=O)C.[Zn]>[CH3:1][C:2]1([CH3:13])[C@H:6]([C:7]#[N:8])[N:5]2[C:9](=[O:12])[C@H:10]([CH:20]([OH:21])[C:19]3[CH:18]=[CH:17][C:16]([N:15]([CH3:14])[CH3:24])=[CH:23][CH:22]=3)[C@H:4]2[S:3]1.[CH3:1][C:2]1([CH3:13])[C@H:6]([C:7]#[N:8])[N:5]2[C:9](=[O:12])[C@@H:10]([CH:20]([OH:21])[C:19]3[CH:18]=[CH:17][C:16]([N:15]([CH3:14])[CH3:24])=[CH:23][CH:22]=3)[C@H:4]2[S:3]1

参加物

7

反応物 2

HCID 74794-(Dimethylamino)BenzaldehydeHCID 129447132,2-Dimethyl-3alpha-cyano-6alpha-bromopenam

生成物 2

HCID 705456532,2-Dimethyl-3alpha-cyano-6alpha-(p-dimethylamino-alpha-hydroxybenzyl)penamHCID 70546902HCID 70546902、化合物

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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## Utilizing 7α-bromo-4-cyano-3-cephem in the above procedure similarly affords 7α-(p-dimethylamino-α-hydroxybenzyl)-4-cyano-3-cephem.

後処理

  1. washwashed with aqueous sodium chloride
  2. dry with materialdried over anhydrous sodium sulfate

出典と根拠

ORDレコード
ord-c52bc1370f8e42859dc572b0280ac4fa
出典データセット
uspto-grants-1981_06
特許番号
US04272439

関連ノート

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