Sodium Chloride → 7beta-Phenoxyacetamido-3-methoxy-ceph-2-em-4alpha-carboxylic acid

HRID 127467Notes

Reaction equation

HRID 127467 reaction equation
[OH-].[K+].C([O:10][C:11]([C@@H:13]1[N:18]2[C:19](=[O:32])[C@@H:20]([NH:21][C:22](=[O:31])[CH2:23][O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C@H:17]2[S:16][CH:15]=[C:14]1[O:33][CH3:34])=[O:12])C1C=CC=CC=1.C(OC(C1N2C(=O)[C@@H](NC(=O)COC3C=CC=CC=3)[C@H]2SCC=1OC)=O)C1C=CC=CC=1.[Cl-].[Na+]>O1CCCC1.C(Cl)Cl>[O:24]([CH2:23][C:22]([NH:21][C@@H:20]1[C:19](=[O:32])[N:18]2[C@@H:13]([C:11]([OH:12])=[O:10])[C:14]([O:33][CH3:34])=[CH:15][S:16][C@H:17]12)=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 14797Potassium HydroxideHCID 128054357beta-Phenoxyacetamido-3-methoxy-ceph-3-em-4-carboxylic acid benzyl esterHCID 705599617beta-Phenoxyacetamido-3-methoxy-ceph-2-em-4alpha-carboxylic acid benzyl ester

Product 1

HCID 128054427beta-Phenoxyacetamido-3-methoxy-ceph-2-em-4alpha-carboxylic acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

15 ml of pre-cooled 0.1 N potassium hydroxide solution are added, whilst stirring, to a solution prepared at 0° C., of 454 mg (1 mmol) of an approx. 3:1 mixture of 7β-phenoxyacetamido-3-methoxy-ceph-2-em-4α-carboxylic acid benzyl ester and 7β-phenoxyacetamido-3-methoxy-ceph-3-em-4-carboxylic acid benzyl ester in 30 ml of tetrahydrofurane. The mixture is stirred for a further 5 minutes at 0° C., 100 ml of ice water and 100 ml of pre-cooled methylene chloride are then added and the whole is stirred vigorously. Addition of a little saturated aqueous sodium chloride solution causes the mixture to separate into two phases. The methylene chloride phase is separated off and the aqueous phase is washed with a further 30 ml of methylene chloride. The aqueous phase is covered with 50 ml of methylene chloride, 10 ml of 2 N hydrochloric acid are added and the mixture is thoroughly shaken. After separating off the organic phase, the aqueous phase is extracted twice more with 30 ml of methylene chloride at a time. The combined methylene chloride extracts are dried over sodium sulphate and concentrated by evaporation in vacuo. The resulting white foam crystallises on addition of chloroform and diethyl ether and gives 7β-phenoxyacetamido-3-methoxy-ceph-2-em-4α-carboxylic acid of melting point 142° C. (decomposition). IR spectrum (KBr): characteristic bands at 5.65, 5.75 and 5.95μ.

Workup

  1. stirringThe mixture is stirred for a further 5 minutes at 0° C.
  2. stirringthe whole is stirred vigorously
  3. customto separate into two phases
  4. customThe methylene chloride phase is separated off
  5. washthe aqueous phase is washed with a further 30 ml of methylene chloride
  6. additionare added
  7. stirringthe mixture is thoroughly shaken
  8. customAfter separating off the organic phase
  9. extractionthe aqueous phase is extracted twice more with 30 ml of methylene chloride at a time
  10. dry with materialThe combined methylene chloride extracts are dried over sodium sulphate
  11. concentrationconcentrated by evaporation in vacuo
  12. customThe resulting white foam crystallises on addition of chloroform and diethyl ether

Sources & evidence

ORD record
ord-d5842d66728a4d3c92e7f9180833ad64
Source dataset
uspto-grants-1981_03
Patent number
US04255328

Reaction notes

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