Toluene → HCID 178520257, compound

HRID 127645Notes

Reaction equation

HRID 127645 reaction equation
C1(C([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:35])[C@@H:24]([NH:25][C:26](=[O:34])[CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C@H:21]3[S:20][CH2:19][C:18]=2[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[S:16])C2C=CC=CC=2)C=CC=CC=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C1(C)C=CC=CC=1>C(Cl)Cl>[C:28]1([CH2:27][C:26]([NH:25][C@@H:24]2[C:23](=[O:35])[N:22]3[C:17]([C:15]([OH:14])=[S:16])=[C:18]([C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=4)[CH2:19][S:20][C@H:21]23)=[O:34])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 131712126HCID 131712126, compound

Product 1

HCID 178520257HCID 178520257, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.96 g (1.62 mmols) of 7β-phenylacetylamino-3-phenylthio-3-cephem-4-carboxylic acid diphenylmethyl ester and 0.26 ml (2.43 mmols) of anisole in 9.6 ml of methylene chloride is stirred with 1.24 ml (16.2 mmols) of trifluoroacetic acid for 30 minutes at 0° C. and the mixture is treated with 50 ml of cold toluene and evaporated in vacuo and the residue is dried in a high vacuum. The residue is digested with diethyl ether, filtered off, rinsed with the same solvent and dried in vacuo. 7β-Phenylacetylamino-3-phenylthio-3-cephem-4-carboxylic acid is obtained as a microcrystalline, colourless powder which can be recrystallised from acetone/methylene chloride/diethyl ether. Melting point 190° C. (decomposition). Thin layer chromatogram (silica gel): Rf ~0.60 (n-butanol/pyridine/acetic acid/H2O, 40:24:6:30); UV spectrum (ethanol): λmax =263 nm (ε=7000); 305 nm (ε=9000); IR spectrum (nujol): characteristic bands at 3.02; 5.59; 5.81; 6.01; 6.22 and 6.48μ.

Workup

  1. customevaporated in vacuo
  2. customthe residue is dried in a high vacuum
  3. filtrationfiltered off
  4. washrinsed with the same solvent
  5. customdried in vacuo

Sources & evidence

ORD record
ord-d0e9536f40364e58b669912f70b6e954
Source dataset
uspto-grants-1981_03
Patent number
US04256739

Reaction notes

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