HCID 23676283, compound → HCID 178502827, compound

HRID 1073822Notes

Reaction equation

HRID 1073822 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.[Na+].[NH:29]([CH2:33][CH2:34][CH2:35][N:36]1[C:40]([SH:41])=[N:39][N:38]=[N:37]1)[C:30]([NH2:32])=[NH:31]>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:41][C:40]4[N:36]([CH2:35][CH2:34][CH2:33][NH:29][C:30]([NH2:32])=[NH:31])[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 23676283HCID 23676283, compoundHCID 1785129801-(3-guanidinopropyl)-5-mercapto-1H-tetrazole

Product 1

HCID 178502827HCID 178502827, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of 363 mg of sodium 7β-[2-(2-aminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-3-hydroxymethyl-3-cephem-4-carboxylate and 241 mg of 1-(3-guanidinopropyl)-5-mercapto-1H-tetrazole in 10 ml of DMF was added 800 mg of ethyl o-phenylenephosphate under stirring at -20° C. The reaction mixture was stirred at -20° C. to 0° C. for 60 minutes and 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 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 294 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 acetonitrile/water (4:1)
  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-48b3a5c972b042b98127092d77838d69
Source dataset
uspto-grants-1990_11
Patent number
US04971963

Reaction notes

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