Lithium Hydroxide → HCID 67036258, compound

HRID 1623493Notes

Reaction equation

HRID 1623493 reaction equation
C[O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=[C:20]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[CH:21]([CH3:23])[CH3:22])[C:12]2=[O:31])[CH:5]=1.[OH-].[Li+]>C1COCC1.O>[Cl:30][C:27]1[CH:26]=[CH:25][C:24]([C:20](=[C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:11]([CH2:10][C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:32])=[O:2])[C:12]2=[O:31])[CH:21]([CH3:23])[CH3:22])=[CH:29][CH:28]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67036257HCID 67036257, compound

Product 1

HCID 67036258HCID 67036258, compoundYield 51.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-{3-[1-(4-chloro-phenyl)-2-methyl-propylidene]-2-oxo-2,3-dihydro-indol-1-ylmethyl}-benzoic acid methyl ester (0.40 g, 0.90 mmol) was dissolved in THF 15 ml. Then a solution of lithium hydroxide (0.38 g, 9.0 mmol) in water (3.0 ml) was added. After stirring for 12 hours, the solvent was removed under reduced pressure. The residue was dissolved in 2 ml DMF for prepared HPLC to give 3-{3-[1-(4-chloro-phenyl)-2-methyl-propylidene]-2-oxo-2,3-dihydro-indol-1-ylmethyl}-benzoic acid as a yellow powder (200 mg). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.00 (d, J=6.82 Hz, 6H) 4.90-4.99 (m, 1H) 5.05 (s, 2H) 5.59 (d, J=7.83 Hz, 1H) 6.64 (t, J=7.71 Hz, 1H) 6.91 (d, J=7.83 Hz, 1H) 7.10 (t, J=7.71 Hz, 1H) 7.27 (d, J=8.34 Hz, 2H) 7.49 (t, J=7.58 Hz, 1H) 7.63 (d, J=8.34 Hz, 2H) 7.59 (d, J=7.58 Hz, 1H) 7.85 (d, J=7.58 Hz, 1H) 7.92 (s, 1H) 13.05 (s, 1H). MS calcd. for C26H22ClNO3 431.5, obsd. (ESI+) [(M+H)+] 432.0.

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in 2 ml DMF
  3. customfor prepared HPLC

Sources & evidence

ORD record
ord-82d8ae6ef2b34fbcb2a6c163abb72a7f
Source dataset
uspto-grants-2014_07
Patent number
US08778973B2

Reaction notes

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