Water → HCID 141573500, compound

HRID 1729559Notes

Reaction equation

HRID 1729559 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:29]/[O:30][CH3:31])/[C:8]([NH:10][CH:11]2[C:27](=[O:28])[N:13]3[C:14]([C:24]([O-:26])=[S:25])=[C:15]([CH2:18][CH:19]4[CH2:23][CH2:22][O:21][CH2:20]4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[Na+].[C:33]([O:39][CH2:40]I)(=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35].O>CN(C)C=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:29]/[O:30][CH3:31])/[C:8]([NH:10][CH:11]2[C:27](=[O:28])[N:13]3[C:14]([C:24]([O:26][CH2:40][O:39][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])=[S:25])=[C:15]([CH2:18][CH:19]4[CH2:23][CH2:22][O:21][CH2:20]4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 104401Iodomethyl pivalateHCID 141573519HCID 141573519, compound

Product 1

HCID 141573500HCID 141573500, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-20 °C

Procedure

Sodium 7-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-(tetrahydrofuran-3-yl)methylthio-3-cephem-4-carboxylate (71 mg) was dissolved in dimethylformamide (1 ml) and the solution was cooled to -20° C. The solution, after addition of iodomethyl pivalate (66 mg) thereto, was stirred at a temeprature of -20° to 10° C. for 30 minutes, after which cold water (10 ml) was added to the reaction solution. The resulting mixture was extracted with ethyl acetate (10 ml) and the organic layer separated was washed with an aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to leave a yellow oil. The oily residue was purifed by a column chromatography on a silica gel column (40 g) with elution using ethyl acetate as eluent to collect fractions containing the titled compound. Concentration of the fractions so collected under reduced pressure gave the titled compound (77 mg; 92%).

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate (10 ml)
  2. customthe organic layer separated
  3. washwas washed with an aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto leave a yellow oil
  7. washThe oily residue was purifed by a column chromatography on a silica gel column (40 g) with elution
  8. customto collect fractions
  9. additioncontaining the titled compound
  10. customConcentration of the fractions so collected under reduced pressure

Sources & evidence

ORD record
ord-d505bd4c11b44dcf924e4aa7f97a4c2d
Source dataset
uspto-grants-1994_07
Patent number
US05332731

Reaction notes

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