Anisole → HCID 131713123, compound

HRID 647120Notes

Reaction equation

HRID 647120 reaction equation
C([O:5][C:6]([CH2:8][O:9][N:10]=[C:11]([C:34]1[N:39]=[C:38]([NH2:40])[CH:37]=[CH:36][N:35]=1)[C:12]([NH:14][CH:15]1[C:32](=[O:33])[N:17]2[C:18]([C:29]([O-:31])=[O:30])=[C:19]([CH2:22][N+:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:20][S:21][C@H:16]12)=[O:13])=[O:7])(C)(C)C.C1(OC)C=CC=CC=1.C(OC(C)C)(C)C>FC(F)(F)C(O)=O>[C:6]([CH2:8][O:9][N:10]=[C:11]([C:34]1[N:39]=[C:38]([NH2:40])[CH:37]=[CH:36][N:35]=1)[C:12]([NH:14][CH:15]1[C:32](=[O:33])[N:17]2[C:18]([C:29]([O-:31])=[O:30])=[C:19]([CH2:22][N+:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:20][S:21][C@H:16]12)=[O:13])([OH:7])=[O:5]

Participants

5

Reactant 3

HCID 7519AnisoleHCID 7914Diisopropyl EtherHCID 131713125HCID 131713125, compound

Product 1

HCID 131713123HCID 131713123, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 7-[2-t-butoxycarbonylmethoxyimino-2-(4-aminopyrimidin-2-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) (1.31 g) and anisole (2.5 ml) in trifluoroacetic acid (7.5 ml) was stirred for 50 minutes under cooling in an ice-bath and for 70 minutes at room temperature. The mixture was poured into cold diisopropyl ether (60 ml) and the resulting precipitates were collected by filtration. The powder was dissolved in water (30 ml) and the mixture was adjusted to pH 4 to 5 with aqueous sodium bicarbonate and subjected to column chromatography on a non ionic adsorption resin "Diaion HP 20" (60 ml). After the column was washed with water, the elution was carried out with 30% aqueous methanol. The eluate was evaporated to remove methanol under reduced pressure and lyophilized to give 7-[2-carboxymethoxyimino-2-[4-aminopyrimidin-2-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) (0.52 g).

Workup

  1. customthe resulting precipitates
  2. filtrationwere collected by filtration
  3. dissolutionThe powder was dissolved in water (30 ml)
  4. washAfter the column was washed with water
  5. washthe elution
  6. customThe eluate was evaporated
  7. customto remove methanol under reduced pressure

Sources & evidence

ORD record
ord-d61eff17d076472d94a7dcfb91a8c66d
Source dataset
uspto-grants-1983_10
Patent number
US04407798

Reaction notes

Loading…