Trifluoroacetic acid → HCID 178496724, compound

HRID 1081563Notes

Reaction equation

HRID 1081563 reaction equation
Br[CH:2]1[C:7]([CH3:8])=[C:6]([C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[O:10])[N:5]2[C:15](=[O:19])[C@H:16]([O:17][CH3:18])[C@H:4]2[S:3]1(=[O:21])=[O:20].C([O:35][C:36]1[C:37](=[O:54])[N:38]=[C:39]([S:43][CH2:44][C:45]2[CH:53]=[CH:52][C:48]([C:49]([OH:51])=[O:50])=[CH:47][CH:46]=2)[N:40]([CH3:42])[N:41]=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>C(#N)C.C(Cl)Cl>[C:11]([C:9]([C:6]1[N:5]2[C:15](=[O:19])[C@H:16]([O:17][CH3:18])[C@H:4]2[S:3](=[O:21])(=[O:20])[CH:2]([O:51][C:49](=[O:50])[C:48]2[CH:52]=[CH:53][C:45]([CH2:44][S:43][C:39]3[N:40]([CH3:42])[N:41]=[C:36]([OH:35])[C:37](=[O:54])[N:38]=3)=[CH:46][CH:47]=2)[C:7]=1[CH3:8])=[O:10])([CH3:14])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 23362766HCID 23362766, compoundHCID 70062891HCID 70062891, compound

Product 1

HCID 178496724HCID 178496724, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-bromo-4-tert-butylcarbonyl-7α-methoxy-3-methyl-3-cephem 1,1-dioxide (110 mg) in acetonitrile (100 ml) was treated with 4-[(6-benzhydryloxy-2,5-dihydro-2-methyl-5-oxo-1,2,4- triazin-3-yl)thiomethyl]benzoic acid siver salt (230 mg). The reaction mixture was stirred at room temperature for 30 minutes, then diluted with EtOAC, filtered and rotoevaporated. Upon purification of the residue by flash chromatography 4-tert-butylcarbonyl-2-{4-[(6-benzhydryloxy-2,5-dihydro-2-methyl-5-oxo-1,2,4-triazin-3-yl)thiomethyl]benzoyloxy}-7α-methoxy-3-methyl-3-cephem 1,1-dioxide was obtained as a white solid (mg 75). This product was dissolved in methylene chloride (0.5 ml) and sequentially treated with anisole (0.03 ml) and trifluoroacetic acid (0.5 ml).

Workup

  1. additiondiluted with EtOAC
  2. filtrationfiltered
  3. customUpon purification of the residue by flash chromatography 4-tert-butylcarbonyl-2-{4-[(6-benzhydryloxy-2,5-dihydro-2-methyl-5-oxo-1,2,4-triazin-3-yl)thiomethyl]benzoyloxy}-7α-methoxy-3-methyl-3-cephem 1,1-dioxide
  4. customwas obtained as a white solid (mg 75)

Sources & evidence

ORD record
ord-db6f8104abbc4e7697703b4551aae18f
Source dataset
uspto-grants-1996_12
Patent number
US05587373

Reaction notes

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