Diethyl Ether → HCID 178480560, compound

HRID 2289044Notes

Reaction equation

HRID 2289044 reaction equation
[N+:1]([C:4]1[CH:57]=[CH:56][C:7]([CH2:8][O:9][C:10]([N:12]=[C:13]([NH:42][C:43]([O:45][CH2:46][C:47]2[CH:52]=[CH:51][C:50]([N+:53]([O-:55])=[O:54])=[CH:49][CH:48]=2)=[O:44])[NH:14][CH2:15][C:16]([NH:18][C@H:19]2[CH2:23][CH2:22][N:21]([C:24]([C@@H:26]3[CH2:30][C@H:29]([S:31]CC4C=CC(OC)=CC=4)[CH2:28][N:27]3[CH3:41])=[O:25])[CH2:20]2)=[O:17])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].FC(F)(F)S(O)(=O)=O.CCOCC>FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>[N+:1]([C:4]1[CH:57]=[CH:56][C:7]([CH2:8][O:9][C:10]([N:12]=[C:13]([NH:42][C:43]([O:45][CH2:46][C:47]2[CH:52]=[CH:51][C:50]([N+:53]([O-:55])=[O:54])=[CH:49][CH:48]=2)=[O:44])[NH:14][CH2:15][C:16]([NH:18][C@H:19]2[CH2:23][CH2:22][N:21]([C:24]([C@@H:26]3[CH2:30][C@H:29]([SH:31])[CH2:28][N:27]3[CH3:41])=[O:25])[CH2:20]2)=[O:17])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 62406Trifluoromethanesulfonic acidHCID 178491728HCID 178491728, compound

Product 1

HCID 178480560HCID 178480560, compoundYield 63.7%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

2.99 g of (2S,4S)-2-[(3S)-3-[2-[2,3-bis(4-nitrobenzyloxycarbonyl)guanidino]acetylanino]pyrrolidin-1-ylcarbonyl]-4-(4-methoxybenzylthio)-1-methylpyrrolidine [prepared as described in step (1) above] were dissolved in a mixture of 21 ml of trifluoroacetic acid and 4.1 ml of anisole, and then 1.15 ml of trifluoromethanesulfonic acid were added dropwise, whilst stirring and ice-cooling, to the resulting solution. The reaction mixture was stirred for 20 minutes at room temperature, after which the mixture was poured into ether. The resulting precipitate was collected by filtration and the precipitate was dissolved in ethyl acetate. The ethyl acetate solution was washed with saturated sodium hydrogencarbonate, with water and with brine and dried over anhydrous sodium sulfate. The ethyl acetate solution was concentrated by evaporation under reduced pressure to obtain 1.62 g of (2S,4S)-2-[(3S)-3-[2-[2,3-bis(4-nitrobenzyloxycarbonyl)guanidino]acetylamino]pyrrolidin-1-ylcarbonyl]-4-mercapto-1-methylpyrrolidine, in the form of an amorphous powder.

Workup

  1. temperatureice-cooling, to the resulting solution
  2. stirringThe reaction mixture was stirred for 20 minutes at room temperature
  3. filtrationThe resulting precipitate was collected by filtration
  4. dissolutionthe precipitate was dissolved in ethyl acetate
  5. washThe ethyl acetate solution was washed with saturated sodium hydrogencarbonate, with water and with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationThe ethyl acetate solution was concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-7fa6fb63f91544beac568ecf3fbee1fa
Source dataset
uspto-grants-2000_07
Patent number
US06090802

Reaction notes

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