Trifluoroacetic acid → 7beta-Phenoxyacetamido-3-methoxy-3-cephem-4-carboxylic acid

HRID 2420546Notes

Reaction equation

HRID 2420546 reaction equation
C1(OC)C=CC=CC=1.C1(C([O:22][C:23]([C:25]2[N:30]3[C:31](=[O:44])[C@@H:32]([NH:33][C:34](=[O:43])[CH2:35][O:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C@H:29]3[S:28][CH2:27][C:26]=2[O:45][CH3:46])=[O:24])C2C=CC=CC=2)C=CC=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[O:36]([CH2:35][C:34]([NH:33][C@@H:32]1[C:31](=[O:44])[N:30]2[C:25]([C:23]([OH:24])=[O:22])=[C:26]([O:45][CH3:46])[CH2:27][S:28][C@H:29]12)=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 6453042Diphenylmethyl (6R-trans)-3-methoxy-8-oxo-7-(phenoxyacetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

Product 1

HCID 127841427beta-Phenoxyacetamido-3-methoxy-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

0.87 ml of anisole is added to a solution of 2.0 g (3.78 mmols) of 7β-phenoxyacetamido-3-methoxy-ceph-3-em-4-carboxylic acid diphenylmethyl ester in 5 ml of methylene chloride and the mixture is cooled to 0° C and, after adding 1.2 ml of trifluoracetic acid, left to stand for 1 hour. The reaction mixture is concentrated in vacuo and the residue is crystallised from acetone/ether. 7β-Phenoxyacetamido-3-methoxy-ceph-3-em-4-carboxylic acid of melting point 170° C (decomposition) is obtained.

Workup

  1. waitleft
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. customthe residue is crystallised from acetone/ether

Sources & evidence

ORD record
ord-9ec472389fec422b8295011d597a5e40
Source dataset
uspto-grants-1978_08
Patent number
US04110533

Reaction notes

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