HCID 178449864, compound → (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[[1-[2-(diaminomethylideneamino)ethyl]tetrazol-5-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1073819Notes

Reaction equation

HRID 1073819 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:25]/[O:26][CH3:27])/[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.C([NH+](CCCC)CCCC)CCC.[NH:41]([CH2:45][CH2:46][N:47]1[C:51]([SH:52])=[N:50][N:49]=[N:48]1)[C:42]([NH2:44])=[NH:43]>CN(C=O)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:25]/[O:26][CH3:27])/[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:52][C:51]4[N:47]([CH2:46][CH2:45][NH:41][C:42]([NH2:44])=[NH:43])[N:48]=[N:49][N:50]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

4

Reactant 2

HCID 178449864HCID 178449864, compoundHCID 178513004HCID 178513004, compound

Product 1

HCID 178502828(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[[1-[2-(diaminomethylideneamino)ethyl]tetrazol-5-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of 559 mg of tributylammonium 7β-[2 -(2-aminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-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 under stirring at -20° C. The reaction mixture was stirred at -20° C. to 0° C. for 90 minutes and 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 the concentrate was subjected to a column chromatography on XAD-II (150 ml), being washed with water and eluted with 10% aqueous ethanol. The eluate was concentrated under reduced pressure and then lyophilized to give 245 mg of the title compound as a colorless powder.

Workup

  1. stirringThe reaction mixture was stirred at -20° C. to 0° C. for 90 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 10% aqueous ethanol
  7. concentrationThe eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b5e532e7105c41e2bed91bc067d24810
Source dataset
uspto-grants-1990_11
Patent number
US04971963

Reaction notes

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