HCID 23662671, compound → HCID 15159513, compound

HRID 1073824Notes

Reaction equation

HRID 1073824 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4](/[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:3]=1.[Na+].[C:30]([CH2:33][S:34][CH2:35][CH2:36][N:37]1[C:41]([SH:42])=[N:40][N:39]=[N:38]1)(=[NH:32])[NH2:31]>CN(C=O)C>[C:30]([CH2:33][S:34][CH2:35][CH2:36][N:37]1[C:41]([S:42][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][CH2:27][CH3:28])[C:23](=[O:24])[N:13]3[C:14]=2[C:20]([OH:22])=[O:21])=[N:40][N:39]=[N:38]1)(=[NH:31])[NH2:32]

Participants

4

Reactant 2

HCID 23662671HCID 23662671, compoundHCID 178512427HCID 178512427, compound

Product 1

HCID 15159513HCID 15159513, compoundYield 31.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of sodium 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-(Z)-2-ethoxyiminoacetamido]-3-hydroxymethyl-3 -cephem-4-carboxylate (360 mg) and 1-(2-amidinomethylthioethyl)-5-mercapto-1H-tetrazole (262 mg) in 8 ml of DMF was added 1.0 g of ethyl o-phenylenephophate under stirring at -20° C. After stirring under ice-cooling for 1.5 hours, the reaction mixture was subjected to a column chromatography (silica gel, 100 g), being washed with acetonitrile and eluted with acetonitrile/water (4:1). The eluate was concentrated under reduced pressure and then subjected to a column chromatography (XAD-II, 150 ml), being washed with water and eluted with 20% aqueous ethanol. The eluate was concentrated under reduced pressure and lyophilized to give 159 mg of the title compound as a colorless powder.

Workup

  1. stirringAfter stirring under ice-
  2. temperaturecooling for 1.5 hours
  3. washbeing washed with acetonitrile
  4. washeluted with acetonitrile/water (4:1)
  5. concentrationThe eluate was concentrated under reduced pressure
  6. washbeing washed with water
  7. washeluted with 20% aqueous ethanol
  8. concentrationThe eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-653375d111c14985b02fb4e24921ae73
Source dataset
uspto-grants-1990_11
Patent number
US04971963

Reaction notes

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