Dimethylacetamide → 7beta-[2-(1H-tetrazol-1-yl)acetamido]-3-(3-oxobutyryloxy)methyl-3-cephem-4-carboxylic acid

HRID 1389679Notes

Reaction equation

HRID 1389679 reaction equation
[NH2:1][C@@H:2]1[C:20](=[O:21])[N:4]2[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH2:9][O:10][C:11](=[O:16])[CH2:12][C:13](=[O:15])[CH3:14])[CH2:7][S:8][C@H:3]12.CN(C)C(=O)C.[N:28]1([CH2:33][C:34](Cl)=[O:35])[CH:32]=[N:31][N:30]=[N:29]1.C(=O)([O-])O.[Na+]>ClCCl>[N:28]1([CH2:33][C:34]([NH:1][C@@H:2]2[C:20](=[O:21])[N:4]3[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH2:9][O:10][C:11](=[O:16])[CH2:12][C:13](=[O:15])[CH3:14])[CH2:7][S:8][C@H:3]23)=[O:35])[CH:32]=[N:31][N:30]=[N:29]1

Participants

6

Reactant 4

HCID 31374DimethylacetamideHCID 516892Sodium BicarbonateHCID 117819897beta-Amino-3(3-oxobutyryloxymethyl)-3-cephem-4-carboxylic acidHCID 13232854(1H-Tetrazol-1-yl)acetyl chloride

Product 1

HCID 705415497beta-[2-(1H-tetrazol-1-yl)acetamido]-3-(3-oxobutyryloxy)methyl-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In dichloromethane (10 ml) was suspended 7β-amino-3-(3-oxobutyryloxy)methyl-3-cephem-4-carboxylic acid (942 mg), followed by the addition of N,N-dimethylacetamide (1 ml). Then, under ice-cooling and stirring, a solution of (1H-tetrazol-1-yl)acetyl chloride (441 mg) in dichloromethane (3 ml) was added. The mixture was further stirred at room temperature for 30 minutes, after which it was poured in an aqueous solution of sodium hydrogen carbonate. The water layer, i.e. aqueous extract, was purified by column-chromatography on Sephadex LH-20. The fractions rich in the desired product were pooled, concentrated, made acidic with phosphoric acid and extracted with ethyl acetate. The extract was dried, concentrated and treated with ether. The procedure provided 7β-[2-(1H-tetrazol-1-yl)acetamido]-3-(3-oxobutyryloxy)methyl-3-cephem-4-carboxylic acid.

Workup

  1. temperatureThen, under ice-cooling
  2. stirringThe mixture was further stirred at room temperature for 30 minutes
  3. customThe water layer, i.e. aqueous extract, was purified by column-chromatography on Sephadex LH-20
  4. concentrationconcentrated
  5. extractionextracted with ethyl acetate
  6. customThe extract was dried
  7. concentrationconcentrated
  8. additiontreated with ether

Sources & evidence

ORD record
ord-0bf0aac5059948e28ba60e19057f76be
Source dataset
uspto-grants-1981_01
Patent number
US04245088

Reaction notes

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