Acetic Acid → Cephaloridine

HRID 1604922Notes

Reaction equation

HRID 1604922 reaction equation
ClC(Cl)C(O[CH2:6][C:7]1[CH2:8][S:9][C@@H:10]2[C@H:17]([NH:18][C:19](=[O:26])[CH2:20][C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)[C:16](=[O:27])[N:11]2[C:12]=1[C:13]([OH:15])=[O:14])=O.[N:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(O)(=O)C>O>[CH:32]1[CH:31]=[CH:30][N+:29]([CH2:6][C:7]2[CH2:8][S:9][C@@H:10]3[C@H:17]([NH:18][C:19]([CH2:20][C:21]4[S:22][CH:23]=[CH:24][CH:25]=4)=[O:26])[C:16](=[O:27])[N:11]3[C:12]=2[C:13]([O-:15])=[O:14])=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1049PyridineHCID 131710126HCID 131710126, compound

Product 1

HCID 5773Cephaloridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Dichloroacetoxymethyl-7β-(2'-thienylacetamido)ceph-3-em-4-carboxylic acid (0.1 g., 2.15 mmole.) was suspended in water (4 ml.), and pyridine (0.352 ml., 4.3 mmole.) was added. The solution was heated at 50° for 1 hour, acidified to pH 4.5 with acetic acid, and washed with ethyl acetate and finally with petrol. The aqueous solution was freed from dissolved organic solvents and applied to a column comprising (from top to bottom) layers of deactivated neutral alumina (8 ml.), Dowex 1 (AcO-) (20 ml.) and Zeokarb 226 (H+) (5 ml.). Elution with water was carried out until the eluate showed no optical rotation; the total eluate was freeze-dried and the residue triturated with methanol to give a white solid (296 mg.), [α]D23 +48.8° (c 0.8, water), λλmax (water) 238nm (E1cm1% = 351), 255 nm (E1cm1% = 324).

Workup

  1. temperatureThe solution was heated at 50° for 1 hour
  2. washwashed with ethyl acetate and finally with petrol
  3. dissolutionfrom dissolved organic solvents
  4. washElution with water
  5. customthe total eluate was freeze-dried
  6. customthe residue triturated with methanol
  7. customto give a white solid (296 mg.), [α]D23 +48.8° (c 0.8, water), λλmax (water) 238nm (E1cm1% = 351), 255 nm (E1cm1% = 324)

Sources & evidence

ORD record
ord-dfd4902f6ef4455695a87b94d1a33da2
Source dataset
uspto-grants-1976_04
Patent number
US03948906

Reaction notes

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