Sulfate Ion → HCID 12911909, compound

HRID 2058508Notes

Reaction equation

HRID 2058508 reaction equation
[O:1]=[C:2]1[C:11]2[C:6]3=[C:7]([CH2:12][CH2:13][N:5]3[CH:4]=[C:3]1[C:14]([OH:16])=O)[CH:8]=[CH:9][CH:10]=2.ClC(OCC(C)C)=O.[CH3:25][C:26]([O:28][CH2:29][C:30]1[CH2:49][S:48][C@@H:33]2[C@H:34]([NH:37][C:38]([C@H:40]([NH2:47])[C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)=[O:39])[C:35](=[O:36])[N:32]2[C:31]=1[C:50]([OH:52])=[O:51])=[O:27].S([O-])([O-])(=O)=O>CN(C)C=O.C(N(CC)CC)C>[O:1]=[C:2]1[C:11]2[C:6]3=[C:7]([CH2:12][CH2:13][N:5]3[CH:4]=[C:3]1[C:14]([NH:47][CH:40]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:38]([NH:37][CH:34]1[C:35](=[O:36])[N:32]3[CH:33]1[S:48][CH2:49][C:30]([CH2:29][O:28][C:26](=[O:27])[CH3:25])=[C:31]3[C:50]([OH:52])=[O:51])=[O:39])=[O:16])[CH:8]=[CH:9][CH:10]=2

Participants

7

Reactant 4

HCID 1117Sulfate IonHCID 19150CephaloglycinHCID 62365Isobutyl chloroformateHCID 755589HCID 755589, compound

Product 1

HCID 12911909HCID 12911909, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent2×

Procedure

2.1 g of 6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acid was added to 50 ml of anhydrous dimethylformamide and 1.66 ml of triethylamine was added to the mixture while ice-cooling and stirred for 15 minutes. Then, 1.6 ml of isobutyl chloroformate was added thereto dropwise and stirred for 45 minutes while ice-cooling. On the other hand, 4.5 g of cephaloglycine was suspended in 60 ml of anhydrous dimethylformamide and 2.8 ml of triethylamine and 1 g of anhydrous sulfate were added to the resulting mixture while ice-cooling followed by stirring the mixture for 30 minutes. Insoluble materials were removed by filtration and the filtrate was added at one time to the former reaction mixture and allowed to react for 2 hours while ice-cooling. After completion of the reaction, insoluble materials were removed by filtration and the filtrate was mixed with 10 ml of a 20% butanol solution of sodium 2-ethylhexanoate followed by the addition of 500 ml of diethyl ether to precipitate crystals. The crystals were collected by filtration and dissolved in 300 ml of water. The resulting solution was rendered acidic (pH=3) with dilute hydrochloric acid to precipitate solid materials, which were washed with water and dried under reduced pressure to obtain 4.0 g of 7-[2-(1,2-dihydro- 6-oxo-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxamido)-2-phenylacetamido]-3-(acetyloxymethyl)-8-oxo-5-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylic acid as white amorphous crystals having a melting point of 245° to 248° C. (decomposition).

Workup

  1. additionwas added to the mixture while ice-
  2. temperaturecooling
  3. stirringdropwise and stirred for 45 minutes while ice-
  4. temperaturecooling
  5. temperaturecooling
  6. stirringby stirring the mixture for 30 minutes
  7. customInsoluble materials were removed by filtration
  8. additionthe filtrate was added at one time to the former reaction mixture
  9. customto react for 2 hours while ice-
  10. temperaturecooling
  11. customAfter completion of the reaction, insoluble materials
  12. customwere removed by filtration
  13. additionthe filtrate was mixed with 10 ml of a 20% butanol solution of sodium 2-ethylhexanoate
  14. additionfollowed by the addition of 500 ml of diethyl ether
  15. customto precipitate crystals
  16. filtrationThe crystals were collected by filtration
  17. dissolutiondissolved in 300 ml of water
  18. customto precipitate solid materials, which
  19. washwere washed with water
  20. customdried under reduced pressure

Sources & evidence

ORD record
ord-491b185b3fbe4a649f76a7b2f7514ce5
Source dataset
uspto-grants-1982_03
Patent number
US04317820

Reaction notes

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