Water → 3-[3-(4-methyl-1-phenyl-pent-(Z)-ylidene)-2-oxo-2,3-dihydro-indol-1-ylmethyl]-benzoic acid

HRID 1623475Notes

Reaction equation

C[O:2][C:3](=[O:33])[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:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)\[CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])/[C:12]2=[O:32])[CH:5]=1.O.O[Li].O>C1COCC1>[CH3:24][CH:23]([CH3:25])[CH2:22][CH2:21]/[C:20](=[C:13]1/[C:12](=[O:32])[N:11]([CH2:10][C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([OH:33])=[O:2])[C:19]2[C:14]/1=[CH:15][CH:16]=[CH:17][CH:18]=2)/[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

Conditions

Temperature: 50 °C

Procedure

3-{3-[4-Methyl-1-phenyl-pent-(Z)-ylidene]-2-oxo-2,3-dihydro-indol-1-ylmethyl}-benzoic acid methyl ester (24 mg, 0.05 mmol) was dissolved in THF (1 ml) and water (1 ml) and LiOH.H2O (14 mg, 0.33 mmol) was added in one portion. The mixture was stirred at 50° C. for 16 h. The mixture was concentrated under reduced pressure and acidified to pH=3. Purification by preparative HPLC afforded 3-[3-(4-methyl-1-phenyl-pent-(Z)-ylidene)-2-oxo-2,3-dihydro-indol-1-ylmethyl]-benzoic acid 10 mg. 1H NMR (300 Hz, CDCl3): δ ppm 0.88 (d, 6H), 1.36-1.44 (m, 2H), 1.64-1.68 (m, 1H), 3.33-3.38 (m, 2H), 5.04 (s, 2H), 6.01 (d, 1H), 6.58-6.61 (m, 2H), 6.96-7.02 (t, 1H), 7.26-7.29 (m, 2H), 7.37 (t, 2H), 7.43-7.52 (m, 3H), 7.93 (d, 1H), 8.03 (s, 1H).

Workup

concentrationThe mixture was concentrated under reduced pressure
customPurification by preparative HPLC

Sources & evidence

ORD record: ord-3e40d30def2b47b298ddbaac0a287a39
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778973B2

Reaction notes

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