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

HRID 26110Notes

Reaction equation

HRID 26110 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 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 5.95 μ.

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-85111c347f2e4c35af4d40e2c34b4ab2
Source dataset
uspto-grants-1979_04
Patent number
US04147864

Reaction notes

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