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Hydrochloric Acid → 7beta-Phenoxyacetamido-3-methoxy-ceph-2-em-4alpha-carboxylic acid

HRID 1155453
Notes
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Reaction equation

HRID 1155453 reaction equation
[OH-].[K+].C[O:4][C:5]([C@@H:7]1[N:12]2[C:13](=[O:26])[C@@H:14]([NH:15][C:16](=[O:25])[CH2:17][O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C@H:11]2[S:10][CH:9]=[C:8]1[O:27][CH3:28])=[O:6].O.Cl>O1CCCC1.C(Cl)Cl>[O:18]([CH2:17][C:16]([NH:15][C@@H:14]1[C:13](=[O:26])[N:12]2[C@@H:7]([C:5]([OH:6])=[O:4])[C:8]([O:27][CH3:28])=[CH:9][S:10][C@H:11]12)=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 705574947beta-Phenoxyacetamido-3-methoxy-ceph-2-em-4alpha-carboxylic acid methyl ester

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344
Dichloromethane
Solvent
HCID 8028TetrahydrofuranSolvent

Procedure

15 ml of cooled 0.1 N aqueous potassium hydroxide solution are added, whilst stirring, to a solution, cooled in an ice bath, of 382 mg of 7β-phenoxyacetamido-3-methoxy-ceph-2-em-4α-carboxylic acid methyl ester in 30 ml of tetrahydrofurane. After 5 minutes, 100 ml of water and 70 ml of methylene chloride are added and the mixture is acidified by adding 10 ml of 1 N aqueous hydrochloric acid. The methylene chloride phase is separated off and the aqueous phase is extracted with 30 ml of methylene chloride. The combined organic phases are dried over sodium sulphate and concentrated by evaporation in vacuo. The residue is crystallised from chloroform/diethyl ether and gives 7β-phenoxyacetamido-3-methoxy-ceph-2-em-4α-carboxylic acid of melting point 142° C. (decomposition).

Workup

  1. customThe methylene chloride phase is separated off
  2. extractionthe aqueous phase is extracted with 30 ml of methylene chloride
  3. dry with materialThe combined organic phases are dried over sodium sulphate
  4. concentrationconcentrated by evaporation in vacuo
  5. customThe residue is crystallised from chloroform/diethyl ether

Sources & evidence

ORD record
ord-c88385ef5e2548b392b70bce18425425
Source dataset
uspto-grants-1981_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04301278

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes