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

HRID 1680128

Reaction equation

HRID 1680128 reaction equation
[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

Participants

7

Reactant 2

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

Product 2

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

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-c52bc1370f8e42859dc572b0280ac4fa
Source dataset
uspto-grants-1981_06
Patent number
US04272439

Linked notes

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