Methanol → Diphenylmethyl 7-amino-3-(benzoxazol-2-yl)thio-3-cephem-4-carboxylate

HRID 974869Notes

Reaction equation

HRID 974869 reaction equation
C1(CC([NH:10][CH:11]2[C:43](=[O:44])[N:13]3[C:14]([C:27]([O:29][CH:30]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[S:28])=[C:15]([C:18]4[O:19][C:20]5[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=5[N:22]=4)[CH2:16][S:17][C@H:12]23)=O)C=CC=CC=1.N1C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl.CO>C(Cl)Cl.O>[NH2:10][CH:11]1[C:43](=[O:44])[N:13]2[C:14]([C:27]([O:29][CH:30]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[S:28])=[C:15]([C:18]3[O:19][C:20]4[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=4[N:22]=3)[CH2:16][S:17][C@H:12]12

Participants

7

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 24819Phosphorus pentachlorideHCID 131719876Diphenylmethyl 7-phenylacetamido-3-(benzoxazol-2-yl)thio-3-cephem-4-carboxylate

Product 1

HCID 131719875Diphenylmethyl 7-amino-3-(benzoxazol-2-yl)thio-3-cephem-4-carboxylateYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-15 °C

Procedure

A 327 mg portion of diphenylmethyl 7-phenylacetamido-3-(benzoxazol-2-yl)thio-3-cephem-4-carboxylate was dissolved in 4 ml of methylene chloride and the resulting solution was cooled to -15° C. To this were added 96 μl of pyridine and 161 mg of phosphorous pentachloride, followed by 1 hour of stirring at -5° C. Next, the reaction solution was cooled down to -20° C., mixed with 1.3 ml of methanol, and then stirred for 3 hours at -5° C. The resulting solution was mixed with 4 ml of water, stirred for additional 1 hour at the same temperature, and then subjected to liquid phase separation. The organic layer was mixed with 4 ml of water, adjusted to pH 7 with saturated sodium bicarbonate aqueous solution and then subjected to liquid phase separation. After drying the resulting organic layer on anhydrous magnesium sulfate and distilling off the solvent under a reduced pressure, the residue was purified by a column chromatography (20 g silica gel, toluene:ethyl acetate =2:1) to obtain 207 mg of the title compound (yield, 78%).

Workup

  1. temperatureNext, the reaction solution was cooled down to -20° C.
  2. stirringstirred for 3 hours at -5° C
  3. stirringstirred for additional 1 hour at the same temperature
  4. customsubjected to liquid phase separation
  5. additionThe organic layer was mixed with 4 ml of water
  6. customsubjected to liquid phase separation
  7. dry with materialAfter drying the resulting organic layer on anhydrous magnesium sulfate
  8. distillationdistilling off the solvent under a reduced pressure
  9. customthe residue was purified by a column chromatography (20 g silica gel, toluene:ethyl acetate =2:1)

Sources & evidence

ORD record
ord-f949d7ca451d4412bca4328b80bcba1c
Source dataset
uspto-grants-1997_03
Patent number
US05607927

Reaction notes

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