Anisole → HCID 131714237, compound

HRID 1247928Notes

Reaction equation

HRID 1247928 reaction equation
[Cl-].[CH2:2]([O:4][N:5]=[C:6]([C:45]1[N:49]=[C:48]([NH2:50])[S:47][N:46]=1)[C:7]([NH:9][CH:10]1[C:43](=[O:44])[N:12]2[C:13]([C:27]([O:29]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:28])=[C:14]([CH2:17][N+:18]3[CH:23]=[CH:22][CH:21]=[C:20]([N:24]([CH3:26])[CH3:25])[CH:19]=3)[CH2:15][S:16][C@H:11]12)=[O:8])[CH3:3].C1(OC)C=CC=CC=1.C(OC(C)C)(C)C>FC(F)(F)C(O)=O>[CH2:2]([O:4][N:5]=[C:6]([C:45]1[N:49]=[C:48]([NH2:50])[S:47][N:46]=1)[C:7]([NH:9][CH:10]1[C:43](=[O:44])[N:12]2[C:13]([C:27]([O-:29])=[O:28])=[C:14]([CH2:17][N+:18]3[CH:23]=[CH:22][CH:21]=[C:20]([N:24]([CH3:26])[CH3:25])[CH:19]=3)[CH2:15][S:16][C@H:11]12)=[O:8])[CH3:3]

Participants

5

Reactant 3

HCID 7519AnisoleHCID 7914Diisopropyl EtherHCID 131714239HCID 131714239, compound

Product 1

HCID 131714237HCID 131714237, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of diphenylmethyl 7-[2-ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-(3-dimethylamino-1-pyridiniomethyl)-3-cephem-4-carboxylate chloride (syn isomer) (0.42 g) and anisole (1 ml) in trifluoroacetic acid (3.5 ml) was stirred for 15 minutes under cooling in an ice bath. The mixture was poured into diisopropyl ether (10 ml) and a resulting precipitate was filtered. The powder was dissolved in water and subjected to column chromatography on a non ionic adsorption resin "Diaion HP 20" (10 ml). After the column was washed with water, the elution was carried out with 30% aqueous methanol. The eluates containing an object compound were collected, evaporated to remove methanol under reduced pressure and lyophilized to give 7-[2-ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-(3-dimethylamino-1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) (0.12 g), mp 129° to 138° C. (dec.).

Workup

  1. temperatureunder cooling in an ice bath
  2. filtrationa resulting precipitate was filtered
  3. dissolutionThe powder was dissolved in water
  4. washAfter the column was washed with water
  5. washthe elution
  6. additionThe eluates containing an object compound
  7. customwere collected
  8. customevaporated
  9. customto remove methanol under reduced pressure

Sources & evidence

ORD record
ord-58d00c2f885a4e5cbd434debb4463b7a
Source dataset
uspto-grants-1985_06
Patent number
US04521413

Reaction notes

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