HCID 13923011, compound → HCID 135967538, compound

HRID 868154Notes

Reaction equation

HRID 868154 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:29][O:30][C:31]([CH3:36])([CH3:35])[C:32]([OH:34])=[O:33])[C:8]([NH:10][CH:11]2[CH2:14][N:13]([C:15]([NH:17][S:18]([N:21]3[CH2:25][CH2:24][N:23]([NH2:26])[C:22]3=[O:27])(=[O:20])=[O:19])=[O:16])[C:12]2=[O:28])=[O:9])[N:6]=1.C[O:38][C:39]1[CH:40]=[C:41]2[C:46](=[CH:47][C:48]=1[O:49]C)[N:45]=[C:44]1[C:51]([O:53][C:54](=[O:55])[C:43]1=[CH:42]2)=[O:52]>CN(C)C=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:29][O:30][C:31]([CH3:36])([CH3:35])[C:32]([OH:34])=[O:33])[C:8]([NH:10][CH:11]2[CH2:14][N:13]([C:15]([NH:17][S:18]([N:21]3[CH2:25][CH2:24][N:23]([NH:26][C:51]([C:44]4[C:43]([C:54]([OH:55])=[O:53])=[CH:42][C:41]5[C:46](=[CH:47][C:48]([OH:49])=[C:39]([OH:38])[CH:40]=5)[N:45]=4)=[O:52])[C:22]3=[O:27])(=[O:19])=[O:20])=[O:16])[C:12]2=[O:28])=[O:9])[N:6]=1

Participants

4

Reactant 2

HCID 13923011HCID 13923011, compoundHCID 54107916HCID 54107916, compound

Product 1

HCID 135967538HCID 135967538, compoundYield 20.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.47 g (0.75 mmol) of 2-[[[1-(2-amino-4-thiazolyl)-2-[[1-[[[[3-amino-2-oxo-1-imidazolidinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]amino]-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid, dipotassium salt in 10 ml of dimethylformamide was added 0.26 g (0.86 mmol) of 6,7-dimethoxy-2,3-quinoline-dicarboxylic anhydride, and the mixture was stirred overnight at room temperature. After the dimethylformamide was distilled off in vacuo, the residue was dissolved in water and the pH adjusted to 6.5 with 1N potassium hydroxide. Freeze drying yielded 0.76 g of crude product which was purified by column chromatography on XAD resin under mplc conditions with water as eluent to give 0.12 g of 2-[[[1-(2-amino-4-thiazolyl)-2-[[1-[[[[3-[[(3-carboxy-6,7-dihydroxy-2-quinolinyl)carbonyl]amino]-2-oxo-1-imidazolidinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]amino]-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid, tripotassium salt, melting point 240°-280° C., dec., and 0.21 g of a mixture of 2-[[[1-(2-amino-4-thiazolyl)-2-[[1-[[[[3-[[ (3-carboxy-6,7-dihydroxy-2-quinolinyl)carbonyl]amino]-2-oxo-1-imidazolidinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]amino]-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid, tripotassium salt and 2-[[[1-(2-amino-4-thiazolyl)-2-[[1-[[[[3-[[(2-carboxy-6,7-dihydroxy-3-quinolinyl)carbonyl]amino]-2-oxo-1-imidazolidinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]amino]-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid, tripotassium salt in a ratio of ca. 2:1.

Workup

  1. distillationAfter the dimethylformamide was distilled off in vacuo
  2. dissolutionthe residue was dissolved in water
  3. customFreeze drying
  4. customyielded 0.76 g of crude product which
  5. customwas purified by column chromatography on XAD resin under mplc conditions with water as eluent

Sources & evidence

ORD record
ord-36507f633feb464ba49f7eea3ec745c4
Source dataset
uspto-grants-1988_10
Patent number
US04777252

Reaction notes

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