1,2-Dichloroethane → HCID 10894519, compound

HRID 727726Notes

Reaction equation

HRID 727726 reaction equation
COC1C=CC(C[S:8][C@@H:9]2[CH2:13][N:12]([CH3:14])[C@H:11]([C:15]([N:17]3[CH2:20][CH:19]([NH:21][C:22]([O:24][CH2:25][C:26]4[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=4)=[O:23])[CH2:18]3)=[O:16])[CH2:10]2)=CC=1.FC(F)(F)C(O)=O.ClCCCl>C1(OC)C=CC=CC=1>[SH:8][C@@H:9]1[CH2:13][N:12]([CH3:14])[C@H:11]([C:15]([N:17]2[CH2:18][CH:19]([NH:21][C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=3)=[O:23])[CH2:20]2)=[O:16])[CH2:10]1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 6422Trifluoroacetic acidHCID 10907392HCID 10907392, compound

Product 1

HCID 10894519HCID 10894519, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

0.73 g of (2S,4S)-4-(4-methoxybenzylthio)-1-methyl-2-[3-(4-nitrobenzyloxycarbonylamino)azetidin-1-ylcarbonyl]pyrrolidine [prepared as described in step (b) above] was dissolved in 1.53 ml of anisole, and 7.25 ml of trifluoroacetic acid and 0.25 ml of trifluoromethanebulfonic acid were added dropwise, whilst ice-cooling, to the resulting solution. The mixture was then stirred at room temperature for 90 minutes, after which 1,2-dichloroethane was added to the reaction mixture and the solvent was removed by evaporation under reduced pressure. The resulting residue was washed by repeated decantation, in turn, with hexane and with diethyl ether. The residue was diluted with ethyl acetate and was made alkaline by the addition of an aqueous solution of sodium hydrogencarbonate. The ethyl acetate layer was washed with water and with an aqueous solution of sodium chloride, in that order, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure, to give 420 mg of the title compound, in the form of an amorphous powder.

Workup

  1. temperaturecooling, to the resulting solution
  2. customthe solvent was removed by evaporation under reduced pressure
  3. washThe resulting residue was washed
  4. additionThe residue was diluted with ethyl acetate
  5. additionby the addition of an aqueous solution of sodium hydrogencarbonate
  6. washThe ethyl acetate layer was washed with water and with an aqueous solution of sodium chloride, in that order
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-b4e36af18b164eef96cbfa7809700dc5
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

Loading…