Succinic anhydride → HCID 70542119, compound

HRID 2285629Notes

Reaction equation

HRID 2285629 reaction equation
C(N(CC)CC)C.[S:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[CH2:13][C:14]([NH:16][C@@H:17]1[C:29](=[O:30])[N:19]2[C:20]([C:26]([OH:28])=[O:27])=[C:21]([CH2:24][OH:25])[CH2:22][S:23][C@H:18]12)=[O:15].[C:31]1(=[O:37])[O:36][C:34](=[O:35])[CH2:33][CH2:32]1>ClCCl>[S:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[CH2:13][C:14]([NH:16][C@@H:17]1[C:29](=[O:30])[N:19]2[C:20]([C:26]([OH:28])=[O:27])=[C:21]([CH2:24][O:25][C:31](=[O:37])[CH2:32][CH2:33][C:34]([OH:36])=[O:35])[CH2:22][S:23][C@H:18]12)=[O:15]

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 70542398HCID 70542398, compound

Product 1

HCID 70542119HCID 70542119, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In dichloromethane (30 ml) was dissolved 7β-(2-thienylacetamido)-3-hydroxymethyl-3-cephem-4-carboxylic acid triethylamine salt (4.55 g), followed by the addition of succinic anhydride (1.50 g). The mixture was stirred at room temperature for 2 hours. The dichloromethane was distilled off and, following the addition of 3% aqueous phosphoric acid solution (100 ml), the residue was extracted with ethyl acetate (150 ml). The ethyl acetate layer was washed with a saturated aqueous solution of sodium chloride (100 ml×2), dried (over magnesium sulfate) and concentrated under reduced pressure. The residue was treated with ether and the resultant powder was recovered by filtration, washed with ether and dried under reduced pressure over phosphorus pentoxide. The procedure provided 7β-(2-thienylacetamido)-3-(3-carboxypropionyloxy)methyl-3-cephem-4-carboxylic acid (4.00 g).

Workup

  1. distillationThe dichloromethane was distilled off
  2. additionthe addition of 3% aqueous phosphoric acid solution (100 ml)
  3. extractionthe residue was extracted with ethyl acetate (150 ml)
  4. washThe ethyl acetate layer was washed with a saturated aqueous solution of sodium chloride (100 ml×2)
  5. dry with materialdried (over magnesium sulfate)
  6. concentrationconcentrated under reduced pressure
  7. additionThe residue was treated with ether
  8. filtrationthe resultant powder was recovered by filtration
  9. washwashed with ether
  10. dry with materialdried under reduced pressure over phosphorus pentoxide

Sources & evidence

ORD record
ord-56752a38a5b344578f0ebfaf99440dca
Source dataset
uspto-grants-1982_04
Patent number
US04323676

Reaction notes

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