sodium (6R,7R)-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetyl]amino]-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate → (6R,7R)-3-[[5-(2-amino-2-iminoethyl)sulfanyl-1,3,4-thiadiazol-2-yl]sulfanylmethyl]-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1073821Notes

Reaction equation

HRID 1073821 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4](/[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:3]=1.[Na+].[C:29]([CH2:32][S:33][C:34]1[S:35][C:36]([SH:39])=[N:37][N:38]=1)(=[NH:31])[NH2:30]>CN(C=O)C>[C:29]([CH2:32][S:33][C:34]1[S:35][C:36]([S:39][CH2:18][C:15]2[CH2:16][S:17][C@@H:12]3[C@H:11]([NH:10][C:8](=[O:9])/[C:7](/[C:4]4[N:3]=[C:2]([NH2:1])[S:6][N:5]=4)=[N:25]\[O:26][CH3:27])[C:23](=[O:24])[N:13]3[C:14]=2[C:20]([OH:22])=[O:21])=[N:37][N:38]=1)(=[NH:30])[NH2:31]

Participants

4

Reactant 2

HCID 23662673sodium (6R,7R)-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetyl]amino]-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateHCID 178512424HCID 178512424, compound

Product 1

HCID 15159481(6R,7R)-3-[[5-(2-amino-2-iminoethyl)sulfanyl-1,3,4-thiadiazol-2-yl]sulfanylmethyl]-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidYield 74.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of 371 mg of sodium 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-(Z)-2-methoxyiminoacetamido]-3-hydroxymethyl-3-cephem-4-carboxylate and 309 mg of 2-amidinomethylthio-5-mercapto-1,3,4-thiadiazole in 10 ml of DMF was added 600 mg of ethyl o-phenylenephosphate under stirring at -20° C. After stirring at -20° C. to 0° C. for 60 minutes, the mixture was subjected to a column chromatography on silica gel (100 g), being washed with acetonitrile and eluted with acetonitrile/water (4:1). The eluate was concentrated under reduced pressure, and the resultant solid was dissolved in dilute hydrochloric acid. This aqueous solution was subjected to a column chromatography on XAD-II (150 ml), being washed with water and eluted with 30% aqueous ethanol. The eluate was concentrated under reduced pressure and lyophilized to give 381 mg of the title compound as a colorless powder.

Workup

  1. stirringAfter stirring at -20° C. to 0° C. for 60 minutes
  2. washbeing washed with acetonitrile
  3. washeluted with acetonitrile/water (4:1)
  4. concentrationThe eluate was concentrated under reduced pressure
  5. dissolutionthe resultant solid was dissolved in dilute hydrochloric acid
  6. washbeing washed with water
  7. washeluted with 30% aqueous ethanol
  8. concentrationThe eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-95ea6496c7ad44c099134f646a8c4a53
Source dataset
uspto-grants-1990_11
Patent number
US04971963

Reaction notes

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