Oxalyl chloride → HCID 54195605, compound

HRID 1380287Notes

Reaction equation

HRID 1380287 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:8]1[S:12][C:11]2[CH:13]=[CH:14][S:15][C:10]=2[CH:9]=1)[C:5](O)=[O:6].C(Cl)(=O)C([Cl:19])=O>C(#N)C.CN(C)C=O>[CH3:1][O:2][N:3]=[C:4]([C:8]1[S:12][C:11]2[CH:13]=[CH:14][S:15][C:10]=2[CH:9]=1)[C:5]([Cl:19])=[O:6]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 54501988HCID 54501988, compound

Product 1

HCID 54195605HCID 54195605, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of 400 mg of α-methoxyimino-α-(thieno[3,2-b]thien-2-yl)acetic acid in 50 ml of acetonitrile containing 15 ml of oxalyl chloride and two drops of N,N-dimethylformamide was stirred at 0° C. for two hours. The reaction mixture was concentrated to dryness by evaporation under reduced pressure to provide α-methoxyimino-α-(thieno[3,2-b]thien-2-yl)acetyl chloride as an oil. The oil was dissolved in 10 ml of fresh acetonitrile and added to a stirred acetonitrile solution of 707 mg of 7-amino-3-methyl-3-cephem-4-carboxylic acid silylated with 2.56 g of bis(trimethylsilyl)trifluoroacetamide (BSTFA). The reaction mixture was stirred at 25° C. for sixteen hours. The reaction mixture was concentrated to dryness to provide an oil which was sonicated for fifteen minutes with 300 ml of saturated aqueous sodium bicarbonate. The mixture was acidified to pH 2.3 by addition of 1N hydrochloric acid. The acid layer was extracted several times with ethyl acetate, and the combined extracts were dried and the solvent was removed by evaporation to provide 970 mg of 7-α-methoxyimino-α-(thieno[3,2-b]thien-2-yl)acetamido-3-methyl-3-cephem-4-carboxylic acid.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness by evaporation under reduced pressure

Sources & evidence

ORD record
ord-b2b94af9e3674f3bb82e05c323c0a9f9
Source dataset
uspto-grants-1986_04
Patent number
US04581352

Reaction notes

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