1,2-Dichloroethane → HCID 178511203, compound

HRID 362110Notes

Reaction equation

HRID 362110 reaction equation
COC1C=CC(C[S:8][C@@H:9]2[CH2:13][N:12]([C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=3)=[O:15])[C@H:11]([C:27]([N:29]3[CH2:32][CH:31]([NH:33][C:34](=[NH:49])[CH2:35][C:36]([O:38][CH2:39][C:40]4[CH:45]=[CH:44][C:43]([N+:46]([O-:48])=[O:47])=[CH:42][CH:41]=4)=[O:37])[CH2:30]3)=[O:28])[CH2:10]2)=CC=1.FC(F)(F)C(O)=O.FC(F)(F)S(O)(=O)=O.ClCCCl>C1(OC)C=CC=CC=1>[SH:8][C@@H:9]1[CH2:13][N:12]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)=[O:15])[C@H:11]([C:27]([N:29]2[CH2:32][CH:31]([NH:33][C:34](=[NH:49])[CH2:35][C:36]([O:38][CH2:39][C:40]3[CH:41]=[CH:42][C:43]([N+:46]([O-:48])=[O:47])=[CH:44][CH:45]=3)=[O:37])[CH2:30]2)=[O:28])[CH2:10]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 178491730HCID 178491730, compound

Product 1

HCID 178511203HCID 178511203, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

0.99 g of (2S, 4S)-4-(4-methoxybenzylthio)-2-[3-(N-4-nitrobenzyloxycarbonylacetimidoylamino)azetidin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine [prepared as described in step (a) above] was dissolved in 1.49 ml of anisole, and 10 ml of trifluoroacetic acid and 0.24 ml of trifluoromethanesulfonic acid were added dropwise to the resulting solution. The resulting mixture was stirred at the same temperature for 40 minutes and then at room temperature for 50 minutes, after which 1,2-dichloroethane was added to the reaction mixture. The mixture was then concentrated by evaporation under reduced pressure. The resulting residue was washed by repeated decantation, in turn, with hexane and diethyl ether, and the mixture was then diluted with ethyl acetate, and 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 0.82 g of the title compound, in the form of an amorphous powder.

Workup

  1. waitat room temperature for 50 minutes
  2. concentrationThe mixture was then concentrated by evaporation under reduced pressure
  3. washThe resulting residue was washed
  4. additionin turn, with hexane and diethyl ether, and the mixture was then 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-b8444aaf3680482aa2a88377ed38fe27
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

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