4-(Dimethylamino)Benzaldehyde → HCID 70545653, Verbindung

HRID 1680128

Reaktionsgleichung

Reaktionsgleichung von HRID 1680128
[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

Komponenten

7

Edukt 2

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

Produkt 2

HCID 70545653HCID 70545653, VerbindungHCID 70546902HCID 70546902, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-c52bc1370f8e42859dc572b0280ac4fa
Quelldatensatz
uspto-grants-1981_06
Patentnummer
US04272439

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