Sodium Bicarbonate → HCID 131710998, compound

HRID 462312Notes

Reaction equation

HRID 462312 reaction equation
[NH2:1][CH:2]1[C:25](=[O:26])[N:4]2[C:5]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[C:6]([CH:9]=[CH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][S:8][C@H:3]12.[CH3:27][C:28]1[CH:29]=CC(S(O)(=O)=O)=C[CH:33]=1.C(=O)(O)[O-].[Na+].C(C(C1C=CC=CC=1)(C(Cl)=O)C(Cl)=O)(C)(C)C.C([C:64]([C:71]1[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=1)([C:68]([OH:70])=O)[C:65]([OH:67])=[O:66])(C)(C)C>C1C=CC=CC=1.C(Cl)(=O)C(Cl)=O.CC(C)=O.O.CN(C)C=O>[C:14]([O:13][C:11]([CH:10]=[CH:9][C:6]1[CH2:7][S:8][C@@H:3]2[CH:2]([NH:1][C:68](=[O:70])[CH:64]([C:65]([O:67][C:28]([CH3:29])([CH3:33])[CH3:27])=[O:66])[C:71]3[CH:72]=[CH:73][CH:74]=[CH:75][CH:76]=3)[C:25](=[O:26])[N:4]2[C:5]=1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:12])([CH3:17])([CH3:16])[CH3:15]

Participants

10

Reactant 4

HCID 516892Sodium BicarbonateHCID 21163678HCID 21163678, compoundHCID 21163742HCID 21163742, compoundHCID 131710999HCID 131710999, compound

Product 1

HCID 131710998HCID 131710998, compound

Reagents, catalysts & solvents 5

HCID 962WaterCatalystHCID 180AcetoneSolvent2×HCID 241BenzeneSolventHCID 6228DimethylformamideSolventHCID 65578Oxalyl chlorideSolvent

Procedure

To a cooled (0°-5° C.) suspension of 277 mg. (0.5 mmole) of tert-butyl 7-amino-3-(2'-tert-butoxycarbonylvinyl)-3-cephem-4-carboxylate-p-toluenesulfonate and 420 mg. (5 equivalents) of sodium bicarbonate in 20 cc. of dry acetone there was added about 1 mmole of tert-butyl phenylmalonic acid chloride (prepared from tert-butyl phenyl malonic acid in benzene plus oxalyl chloride and a trace of dimethylformamide [DMF] in acetone). After 10 minutes at 0°-5° C. and one and one-half hours at room temperature, the reaction mixture was re-cooled to 0° C. to 5° C. and a few drops of water was added. After ten minutes this minute was evaporated under reduced pressure to dryness, the residue was taken up in ethyl acetate, the ethyl acetate solution was washed twice with cold 5 percent hydrochloric acid, with saturated aqueous sodium bicarbonate solution, with saturated aqueous sodium chloride solution, and then dried over magnesium sulfate, filtered and evaporated under reduced pressure. The oily tert-butyl 3-(2'-tert-butoxycarbonylvinyl)-7-(2'-tert-butoxycarbonyl-2'-phenylacetamido)-3-cephem-4-carboxylate ester was chromatographed over silica gel 15 percent water and eluted with 2 percent ethyl acetate in benzene. This title ester material crystallized from ethyl ether in the cold, m.p. 168°-170° C. and was characterized by IR, UV [λmax = 317 inμ (ε = 23,000)] and by elemental analysis which follows.

Workup

  1. temperatureTo a cooled
  2. addition(0°-5° C.) suspension of 277 mg
  3. customAfter ten minutes this minute was evaporated under reduced pressure to dryness
  4. washthe ethyl acetate solution was washed twice with cold 5 percent hydrochloric acid, with saturated aqueous sodium bicarbonate solution, with saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe oily tert-butyl 3-(2'-tert-butoxycarbonylvinyl)-7-(2'-tert-butoxycarbonyl-2'-phenylacetamido)-3-cephem-4-carboxylate ester was chromatographed over silica gel 15 percent water
  9. washeluted with 2 percent ethyl acetate in benzene
  10. customThis title ester material crystallized from ethyl ether in the cold, m.p. 168°-170° C.

Sources & evidence

ORD record
ord-3e909d16385e478b8da569c3a7cb41f9
Source dataset
uspto-grants-1977_12
Patent number
US04065620

Reaction notes

Loading…