HCID 178474910, compound → HCID 178474911, compound

HRID 1073820Notes

Reaction equation

HRID 1073820 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:25]/[O:26][CH2:27][CH3:28])/[C:8]([NH:10][C@@H:11]2[C:23](=[O:24])[N:13]3[C:14]([C:20]([O-:22])=[O:21])=[C:15]([CH2:18]O)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[Na+].[NH:30]([CH2:34][CH2:35][N:36]1[C:40]([SH:41])=[N:39][N:38]=[N:37]1)[C:31]([NH2:33])=[NH:32]>CN(C=O)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:25]/[O:26][CH2:27][CH3:28])/[C:8]([NH:10][C@@H:11]2[C:23](=[O:24])[N:13]3[C:14]([C:20]([OH:22])=[O:21])=[C:15]([CH2:18][S:41][C:40]4[N:36]([CH2:35][CH2:34][NH:30][C:31]([NH2:33])=[NH:32])[N:37]=[N:38][N:39]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

4

Reactant 2

HCID 178474910HCID 178474910, compoundHCID 178513004HCID 178513004, compound

Product 1

HCID 178474911HCID 178474911, compoundYield 53.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 467 mg of sodium 7β-[2-(2-aminothiazol-4-yl)-(Z)-2-ethoxyiminoacetamido]-3-hydroxymethyl -3-cephem-4-carboxylate and 374 mg of 1-(2-guanidinoethyl) -5-mercapto-1H-tetrazole in 10 ml of DMF was added 500 mg of ethyl o-phenylenephosphate at -20° C. under stirring. The reaction mixture was stirred at -20° C. to 0° C. for 60 minutes, and was subjected to a column chromatography on silica gel (100 g), being washed with acetonitrile and eluted with a (5:1) mixture of acetonitrile and water. The eluate was concentrated under reduced pressure, and then subjected to a column chromatography on XAD-II (150 ml), being washed with water and eluted with 20% aqueous ethanol. The eluate was concentrated under reduced pressure and then lyophilized to give 333 mg of the title compound as a colorless powder.

Workup

  1. stirringThe reaction mixture was stirred at -20° C. to 0° C. for 60 minutes
  2. washbeing washed with acetonitrile
  3. washeluted with a (5:1) mixture of acetonitrile and water
  4. concentrationThe eluate was concentrated under reduced pressure
  5. washbeing washed with water
  6. washeluted with 20% aqueous ethanol
  7. concentrationThe eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-dcfc11b3d7644a4da7095ede8de50844
Source dataset
uspto-grants-1990_11
Patent number
US04971963

Reaction notes

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