Trifluoroacetic acid → (E)-2-(4-Chlorophenyl)-N-{(3S)-1-[(1S)-1-methyl-2-oxo-2-piperidin-1-ylethyl]-2-oxopyrrolidin-3-yl}ethenesulfonamide

HRID 7299Notes

Reaction equation

HRID 7299 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[S:10]([NH:13][C@H:14]2[CH2:18][CH2:17][N:16]([C@@H:19]([CH3:27])[C:20](OC(C)(C)C)=[O:21])[C:15]2=[O:28])(=[O:12])=[O:11])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.Cl.CN(C)CCCN=C=NCC.[CH:48]1[CH:49]=[CH:50]C2N(O)N=[N:54][C:52]=2[CH:53]=1.N1CCCCC1>C(Cl)Cl.C(N(CC)CC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[S:10]([NH:13][C@H:14]2[CH2:18][CH2:17][N:16]([C@@H:19]([CH3:27])[C:20](=[O:21])[N:54]3[CH2:50][CH2:49][CH2:48][CH2:53][CH2:52]3)[C:15]2=[O:28])(=[O:11])=[O:12])=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 8082PiperidineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69224557HCID 69224557, compound

Product 1

HCID 10138121(E)-2-(4-Chlorophenyl)-N-{(3S)-1-[(1S)-1-methyl-2-oxo-2-piperidin-1-ylethyl]-2-oxopyrrolidin-3-yl}ethenesulfonamideYield 21.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

tert-Butyl (2S)-2-[(3S)-3-({[(E)-2-(4-chlorophenyl)ethenyl]sulfonyl}amino)-2-oxopyrrolidin-1-yl]propanoate (0.192 g) was dissolved in DCM (2 ml) and treated with trifluoroacetic acid (2 ml) and stirred at room temperature for 2 h. The mixture was then concentrated under reduced pressure to give an oil which was subsequently dissolved in DCM (5 ml) and treated with 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.256 g), HOBT (0.184 g) and triethylamine (0.375 ml). After the solution had been stirred at room temperature for 30 min, piperidine (0.133 ml) was added and the resultant mixture stirred for a further 20 h. The mixture was concentrated under reduced pressure and the residue partitioned between DCM and water. The organic component was washed with water and brine, and concentrated under reduced pressure. The residue was purified using SPE (silica, eluting with cyclohexane; cyclohexane:ethyl acetate 4:1, 1:1, 1:4; ethyl acetate; methanol:ethyl acetate 1:10; methanol) to give the title compound (0.042 g) as a white solid.

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. customto give an oil which
  3. stirringAfter the solution had been stirred at room temperature for 30 min
  4. concentrationThe mixture was concentrated under reduced pressure
  5. customthe residue partitioned between DCM and water
  6. washThe organic component was washed with water and brine
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified
  9. washSPE (silica, eluting with cyclohexane; cyclohexane:ethyl acetate 4:1, 1:1, 1:4; ethyl acetate; methanol:ethyl acetate 1:10; methanol)

Sources & evidence

ORD record
ord-7fc146245d2646ceb6e43fdc8a567d2e
Source dataset
uspto-grants-2006_08
Patent number
US07084139B2

Reaction notes

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