Furan → HCID 131709924, compound

HRID 1580491Notes

Reaction equation

HRID 1580491 reaction equation
C(O[CH2:5][C:6]1[CH:11]([C:12]([OH:14])=[O:13])[N:10]2[C:15](=[O:27])[CH:16]([NH:17][C:18](=[O:26])[CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C@H:9]2[S:8][CH:7]=1)(=O)C.[O:28]1[CH:32]=[CH:31][CH:30]=[CH:29]1>FC(F)(F)C(O)=O.C1(C)C=CC=CC=1>[CH2:5]([C:6]1[CH:11]([C:12]([OH:14])=[O:13])[N:10]2[C:15](=[O:27])[CH:16]([NH:17][C:18](=[O:26])[CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[C@H:9]2[S:8][CH:7]=1)[C:32]1[O:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 2

HCID 8029FuranHCID 131709916HCID 131709916, compound

Product 1

HCID 131709924HCID 131709924, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

0.04 g of 3-acetoxymethyl-7-(N-phenylacetyl-amino)-ceph-2-em-4ξ-carboxylic acid and 0.027 g of furane are simultaneously dissolved in 2 ml of trifluoroacetic acid; the solution is left to stand for 15 minutes at room temperature and is then diluted with an equal volume of toluene. The mixture is evaporated to dryness under reduced pressure and the residue is worked up in accordance with the process described in example 6. 3-Furfuryl-7-(N-phenylacetyl-amino)-ceph-2-em-4ξ-carboxylic acid is thus obtained, showing the following Rf values in a thin layer chromatogram (silica gel): 0.75 (system n-butanol/acetic acid/water, 67:10:23) and 0.52 (system n-butanol/ethanol/water, 40:10:50).

Workup

  1. waitthe solution is left
  2. customThe mixture is evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-5dddc6da22c343ab86b4cca48941fd08
Source dataset
uspto-grants-1976_01
Patent number
US03932465

Reaction notes

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