Toluene → HCID 131709923, compound

HRID 1580490Notes

Reaction equation

HRID 1580490 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.C(O[CH2:10][C:11]1[CH:16]([C:17]([OH:19])=[O:18])[N:15]2[C:20](=[O:32])[CH:21]([NH:22][C:23](=[O:31])[CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C@H:14]2[S:13][CH:12]=1)(=O)C.C1(C)C=CC=CC=1>FC(F)(F)C(O)=O>[C:25]1([CH2:24][C:23]([NH:22][CH:21]2[C:20](=[O:32])[N:15]3[CH:16]([C:17]([OH:19])=[O:18])[C:11]([CH2:10][C:5]4[S:1][CH:2]=[CH:3][CH:4]=4)=[CH:12][S:13][C@H:14]23)=[O:31])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 8030ThiopheneHCID 131709916HCID 131709916, compound

Product 1

HCID 131709923HCID 131709923, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 3.4 g of thiophene in 200 ml of trifluoroacetic acid is mixed with 4 g of 3-acetoxymethyl-7-(N-phenylacetyl-amino)-ceph-2-em-4ξ-carboxylic acid and the solution is left to stand for 15 minutes at room temperature and then mixed with an equal quantity of toluene, and the mixture is evaporated under reduced pressure. The residue is triturated with acetic acid ethyl ester and the solid material is twice crystallised from a mixture of methanol and acetic acid ethyl ester. 7-(N-Phenylacetyl-amino)-3-(2-thenyl)-ceph-2-em-4ξ-carboxylic acid is thus obtained as colourless crystals, melting point 189°C; thin layer chromatogram (silica gel): Rf = 0.72 (system n-butanol/acetic acid/water, 75:7.5:21), Rf = 0.81 (system n-butanol/acetic acid/water, 67:10:23) and Rf = 0.50 (system n-butanol/ethanol/water, 40:10:50); ultraviolet absorption spectrum (in methanol):λmax = 233 mμ (ε = 15400); infrared absorption spectrum (in mineral oil): characteristic bands at 3.01μ, 5.73μ, 5.82μ and 6.05μ. A further quantity of the desired product can be obtained by concentrating the mother liquor and recrystallising the crystalline material.

Workup

  1. waitthe solution is left
  2. customthe mixture is evaporated under reduced pressure
  3. customThe residue is triturated with acetic acid ethyl ester
  4. customthe solid material is twice crystallised from a mixture of methanol and acetic acid ethyl ester

Sources & evidence

ORD record
ord-fadf08177a82407c9aa888fbc7e07483
Source dataset
uspto-grants-1976_01
Patent number
US03932465

Reaction notes

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