Dimethylacetamide → HCID 131712063, compound

HRID 1389678Notes

Reaction equation

HRID 1389678 reaction equation
[NH2:1][C@@H:2]1[C:21](=[O:22])[N:4]2[C:5]([C:18]([OH:20])=[O:19])=[C:6]([CH2:9][O:10][C:11](=[O:17])[CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH2:7][S:8][C@H:3]12.CN(C)C(=O)C.[N:29]1([CH2:34][C:35](Cl)=[O:36])[CH:33]=[N:32][N:31]=[N:30]1.C(=O)([O-])O.[Na+:42]>ClCCl>[Na+:42].[Na+:42].[N:29]1([CH2:34][C:35]([NH:1][C@@H:2]2[C:21](=[O:22])[N:4]3[C:5]([C:18]([O-:20])=[O:19])=[C:6]([CH2:9][O:10][C:11](=[O:17])[CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH2:7][S:8][C@H:3]23)=[O:36])[CH:33]=[N:32][N:31]=[N:30]1.[N:29]1([CH2:34][C:35]([NH:1][C@@H:2]2[C:21](=[O:22])[N:4]3[C:5]([C:18]([O-:20])=[O:19])=[C:6]([CH2:9][O:10][C:11](=[O:17])[CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH2:7][S:8][C@H:3]23)=[O:36])[CH:33]=[N:32][N:31]=[N:30]1

Participants

6

Reactant 4

HCID 31374DimethylacetamideHCID 516892Sodium BicarbonateHCID 13232854(1H-Tetrazol-1-yl)acetyl chlorideHCID 70543657HCID 70543657, compound

Product 1

HCID 131712063HCID 131712063, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In dichloromethane (7 ml) was suspended 7β-amino-3-(3-carboxypropionyloxy)methyl-3-cephem-4-carboxylic acid (660 mg), followed by the addition of N,N-dimethylacetamide (0.7 ml). Then, under ice-cooling and stirring, a solution of (1H-tetrazol-1-yl)acetyl chloride (294 mg) in dichloromethane (2 ml) was added. The mixture was stirred at room temperature for 1 hour, after which time it was poured in an aqueous solution of sodium hydrogen carbonate and separated. The water layer was taken, washed with dichloromethane, made acidic with phosphoric acid and extracted with ethyl acetate. The extract was re-extracted with aqueous sodium hydrogen carbonate solution to bring the desired compound into the aqueous phase. This aqueous solution was purified by column-chromatography on Sephadex LH-20. The fractions containing the dominant product were pooled and lyophilized. The procedure provided 7β-[2-(1H-tetrazol-1-yl)acetamido]-3-(3-carboxypropionyloxy)methyl-3-cephem-4-carboxylic acid disodium salt.

Workup

  1. temperatureThen, under ice-cooling
  2. stirringThe mixture was stirred at room temperature for 1 hour
  3. customseparated
  4. washwashed with dichloromethane
  5. extractionextracted with ethyl acetate
  6. extractionThe extract was re-extracted with aqueous sodium hydrogen carbonate solution
  7. customThis aqueous solution was purified by column-chromatography on Sephadex LH-20
  8. additionThe fractions containing the dominant product

Sources & evidence

ORD record
ord-dec427d519c3485dabf1b296ffec05a4
Source dataset
uspto-grants-1981_01
Patent number
US04245088

Reaction notes

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