Trifluoroacetic acid → (E)-N1-(3-(1H-imidazol-1-yl)propyl)-N8-hydroxy-2-((naphthalen-1-yloxy)methyl)octenediamide

HRID 555360

Reaction equation

HRID 555360 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:39])/[C:11](/[CH2:27][O:28][C:29]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH:32]=[CH:31][CH:30]=2)=[CH:12]/[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([NH:19][O:20]C2CCCCO2)=[O:18])[CH:5]=[CH:4][N:3]=[CH:2]1.FC(F)(F)C(O)=O.CO.ClCCl>CO>[N:1]1([CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:39])/[C:11](/[CH2:27][O:28][C:29]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH:32]=[CH:31][CH:30]=2)=[CH:12]/[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([NH:19][OH:20])=[O:18])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 21226129Dichloromethane methanolHCID 86640100(E)-N1-(3-(1H-imidazol-1-yl)propyl)-2-((naphthalen-1-yloxy)methyl)-N8-(tetra hydro-2H-pyran-2-yloxy)-2-octenediamide

Product 1

HCID 16117444(E)-N1-(3-(1H-imidazol-1-yl)propyl)-N8-hydroxy-2-((naphthalen-1-yloxy)methyl)octenediamideYield 37%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(E)-N1-(3-(1H-imidazol-1-yl)propyl)-2-((naphthalen-1-yloxy)-methyl)-N8-(tetrahydro-2H-pyran-2-yloxy)-2-octenediamide (203 mg, 0.38 mM) obtained in Example (2-1-3) was dissolved in methanol (2 ml), and trifluoroacetic acid (146 μl, 1.90 mM) was slowly added thereto at 0° C. Then, the resulting mixture was heated to room temperature and reacted for 18 hrs. After the completion of reaction, the solvent was removed under reduced pressure. The residue thus obtained was subjected to a silica gel column chromatography (eluent: methanol/dichloromethane=1/9) to obtain 63 mg of the title compound (yield 37%).

Workup

  1. customat 0° C
  2. customreacted for 18 hrs
  3. customAfter the completion of reaction
  4. customthe solvent was removed under reduced pressure
  5. customThe residue thus obtained

Sources & evidence

ORD record
ord-e28a77b847124935a30960ddb6b8fa2e
Source dataset
uspto-grants-2011_11
Patent number
US08053435B2

Linked notes

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