Trifluoroacetic acid → HCID 86751990, compound

HRID 362024Notes

Reaction equation

HRID 362024 reaction equation
FC(F)(F)C(O)=O.FC(F)(F)S(O)(=O)=O.COC1C=CC(C[S:23][C@@H:24]2[CH2:28][N:27]([C:29]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=3)=[O:30])[C@H:26]([C:42]([N:44]3[CH2:49][CH2:48][N:47]([C:50]([O:52][CH2:53][C:54]4[CH:59]=[CH:58][C:57]([N+:60]([O-:62])=[O:61])=[CH:56][CH:55]=4)=[O:51])[CH2:46][CH:45]3[CH3:63])=[O:43])[CH2:25]2)=CC=1>C1(OC)C=CC=CC=1>[SH:23][C@@H:24]1[CH2:28][N:27]([C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=2)=[O:30])[C@H:26]([C:42]([N:44]2[CH2:49][CH2:48][N:47]([C:50]([O:52][CH2:53][C:54]3[CH:55]=[CH:56][C:57]([N+:60]([O-:62])=[O:61])=[CH:58][CH:59]=3)=[O:51])[CH2:46][CH:45]2[CH3:63])=[O:43])[CH2:25]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 22881641HCID 22881641, compound

Product 1

HCID 86751990HCID 86751990, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

23 ml of trifluoroacetic acid, followed by 0.57 ml of trifluoromethanesulfonic acid, were added dropwise to a solution of 2.26 g of (2S,4S)-4-(4-methoxybenzylthio)-2-[2-methyl-4-(4-nitrobenzyloxycarbonyl)piperazin-1-yl-carbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine [prepared as described in step (iii) above] in 3.48 ml of anisole, and the resulting mixture was worked up and purified by the same procedure as described in Preparation 4(ii), to give 1.88 g of the title compound, as an amorphous solid.

Workup

  1. custompurified by the same procedure
  2. customas described in Preparation 4(ii)

Sources & evidence

ORD record
ord-42e15a2a7ead4be7bf745a118fcf4644
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

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