Diisopropyl Ether → HCID 178418649, compound

HRID 5530Notes

Reaction equation

HRID 5530 reaction equation
[OH:1][C:2]1[C:7]([OH:8])=[CH:6][N:5]=[C:4]([C:9]([OH:11])=O)[CH:3]=1.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:37][C:38]1[S:42][N:41]=[C:40]([C:43](=[N:67][O:68][CH3:69])[C:44]([NH:46][C@@H:47]2[C:65](=[O:66])[N:49]3[C:50]([C:62]([O-:64])=[O:63])=[C:51]([CH2:54][N+:55]4([CH3:61])[CH2:60][CH2:59][NH:58][CH2:57][CH2:56]4)[CH2:52][S:53][C@H:48]23)=[O:45])[N:39]=1.C[Si](C)(C)NC(=O)C.C(OC(C)C)(C)C>CS(C)=O>[NH2:37][C:38]1[S:42][N:41]=[C:40]([C:43](=[N:67][O:68][CH3:69])[C:44]([NH:46][C@@H:47]2[C:65](=[O:66])[N:49]3[C:50]([C:62]([O-:64])=[O:63])=[C:51]([CH2:54][N+:55]4([CH3:61])[CH2:60][CH2:59][N:58]([C:9]([C:4]5[CH:3]=[C:2]([OH:1])[C:7]([OH:8])=[CH:6][N:5]=5)=[O:11])[CH2:57][CH2:56]4)[CH2:52][S:53][C@H:48]23)=[O:45])[N:39]=1

Participants

8

Reactant 6

HCID 7914Diisopropyl EtherHCID 10868DicyclohexylcarbodiimideHCID 25989Acetamide, N-(trimethylsilyl)-HCID 757711-HydroxybenzotriazoleHCID 1317181317beta-[2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetamido]-3-(1-methyl-1-piperazinio)methyl-3-cephem-4-carboxylateHCID 178418665HCID 178418665, compound

Product 1

HCID 178418649HCID 178418649, compoundYield 3.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of 4,5-dihydroxy-2-pyridinecarboxylic acid (3.1 g) and 1-hydroxybenzotriazole (4.0 g) in dimethyl sulfoxide (30 ml) was added N,N'-dicyclohexylcarbodiimide (6.2 g). After being stirred at room temperature for 1 hour, the reaction mixture was added to a solution of 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetamido]-3-(1-methyl-1-piperazinio)methyl-3-cephem-4-carboxylate (syn isomer) (10.0 g) and N-trimethylsilylacetamide (3.0 g) in dimethyl sulfoxide (50 ml), and the stirring was continued for 30 minutes. The mixture was added dropwise to diisopropyl ether (1.5 l) and the resulting precipitate was collected by filtration, which was dissolved in an aqueous solution of sodium bicarbonate. After the insoluble material was filtered off, the filtrate was adjusted to pH 3.0 with 1N hydrochloric acid and subjected to column chromatography on "Diaion HP-20" with 5% aqueous isopropyl alcohol as an eluent. The eluate was lyophilized to give 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetamido]-3-[1-methyl-4-(4,5-dihydroxy-2-pyridylcarbonyl)-1-piperazinio]methyl-3-cephem-4-carboxylate (syn isomer) (0.5 g).

Workup

  1. waitthe stirring was continued for 30 minutes
  2. filtrationthe resulting precipitate was collected by filtration, which
  3. dissolutionwas dissolved in an aqueous solution of sodium bicarbonate
  4. filtrationAfter the insoluble material was filtered off

Sources & evidence

ORD record
ord-d576ec8dc5e942d7a4fd333adedd0dc3
Source dataset
uspto-grants-1993_09
Patent number
US05244890

Reaction notes

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