Trifluoroacetic acid → N-[(3s)-1-{(2s)-1-[(3s)-3-Aminopiperidin-1-Yl]-1-Oxopropan-2-Yl}-2-Oxopyrrolidin-3-Yl]-6-Chloronaphthalene-2-Sulfonamide

HRID 7319Notes

Reaction equation

HRID 7319 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([NH:15][C@H:16]1[CH2:20][CH2:19][N:18]([C@@H:21]([CH3:41])[C:22]([N:24]3[CH2:29][CH2:28][CH2:27][C@H:26]([NH:30]C(=O)OCC4C=CC=CC=4)[CH2:25]3)=[O:23])[C:17]1=[O:42])(=[O:14])=[O:13])[CH:6]=[CH:5]2.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:30][C@H:26]1[CH2:27][CH2:28][CH2:29][N:24]([C:22](=[O:23])[C@@H:21]([N:18]2[CH2:19][CH2:20][C@H:16]([NH:15][S:12]([C:7]3[CH:6]=[CH:5][C:4]4[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=4)[CH:8]=3)(=[O:14])=[O:13])[C:17]2=[O:42])[CH3:41])[CH2:25]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86593862Benzyl (3S)-1-[(2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoyl]piperidin-3-ylcarbamate

Product 1

HCID 69329865N-[(3s)-1-{(2s)-1-[(3s)-3-Aminopiperidin-1-Yl]-1-Oxopropan-2-Yl}-2-Oxopyrrolidin-3-Yl]-6-Chloronaphthalene-2-SulfonamideYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl (3S)-1-[(2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoyl]piperidin-3-ylcarbamate (0.128 g) was dissolved in DCM (3.5 ml) and treated with trifluoroacetic acid (10.5 ml) and stirred at room temperature for 6 h. The mixture was concentrated under reduced pressure and the residue purified by SPE (acid ion-exchange, eluting with ethyl acetate:methanol 9:1) to give the title compound (0.093 g) as a colourless oil.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue purified by SPE (acid ion-exchange, eluting with ethyl acetate:methanol 9:1)

Sources & evidence

ORD record
ord-81c46fc548a2432dba9495e6a550bdcd
Source dataset
uspto-grants-2006_08
Patent number
US07084139B2

Reaction notes

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