Lithium Hydroxide → HCID 67244290, compound

HRID 2422544Notes

Reaction equation

HRID 2422544 reaction equation
[N+](C1C=CC(C([O:10][C@@:11]([C:18]2[N:19]=[N:20][N:21]([CH2:23][C:24]3[CH:33]=[C:32]4[C:27]([C:28]([C:36](=[O:38])[CH3:37])=[CH:29][C:30]([C:34]#[N:35])=[N:31]4)=[CH:26][CH:25]=3)[CH:22]=2)([C:14]([F:17])([F:16])[F:15])[CH2:12][CH3:13])=O)=CC=1)([O-])=O.[OH-].[Li+]>C1COCC1.C(OCC)(=O)C>[C:36]([C:28]1[C:27]2[C:32](=[CH:33][C:24]([CH2:23][N:21]3[CH:22]=[C:18]([C@:11]([OH:10])([C:14]([F:15])([F:16])[F:17])[CH2:12][CH3:13])[N:19]=[N:20]3)=[CH:25][CH:26]=2)[N:31]=[C:30]([C:34]#[N:35])[CH:29]=1)(=[O:38])[CH3:37]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 66791320HCID 66791320, compound

Product 1

HCID 67244290HCID 67244290, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-1-{1-[(4-acetyl-2-cyanoquinolin-7-yl)methyl]-1H-1,2,3-triazol-4-yl}-1-(trifluoromethyl)propyl 4-nitrobenzoate (obtained as described in Example 52, step 4) (47 mg, 0.085 mmol) in THF (2 mL) was added lithium hydroxide 2M (210 uL, 0.42 mmol). The mixture was stirred at room temperature for 2 h. The reaction mixture was then diluted with ethyl acetate, washed with an ammonium chloride sln., brine, dried over MgSO4, filtered and concentrated to yield the title compound. The crude residue was purified by flash chromatography (10% acetone-90% dichloromethane) to give the desired product. 1H NMR (400 MHz, acetone-d6): δ 8.55 (d, 1H), 8.40 (s, 1H), 8.24 (s, 1H), 8.11 (s, 1H), 8.85 (d, 1H), 6.02 (s, 2H), 2.85 (s, 3H), 2.35 (m, 1H), 2.05 (m, 1H), 0.86 (t, 3H).

Workup

  1. washwashed with an ammonium chloride sln
  2. dry with material, brine, dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c74ff6325de84b429e1b6667f86f40ef
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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