Lithium Hydroxide → HCID 59263366, compound

HRID 645280Notes

Reaction equation

HRID 645280 reaction equation
[CH2:1]([N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH2:26][C:27]([O-:29])=[O:28])([C:16]2[C:24](O)=[CH:23][C:19]3[O:20][CH2:21][O:22][C:18]=3[CH:17]=2)[C:8]1=[O:30])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[OH-].[Li+]>C1COCC1.O>[CH2:1]([N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]2([C:16]3[CH:17]=[C:18]4[O:22][CH2:21][O:20][C:19]4=[CH:23][C:24]=3[O:29][C:27](=[O:28])[CH2:26]2)[C:8]1=[O:30])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86609021HCID 86609021, compound

Product 1

HCID 59263366HCID 59263366, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 2-(1-hexyl-3-(6-hydroxybenzo[d][1,3]dioxol-5-yl)-2-oxoindolin-3-yl)acetate (0.19 g, 0.43 mmol) in THF:H2O (2:1) was added lithium hydroxide (0.04 g, 0.86 mmol). The mixture was stirred at ambient temperature for 4 hrs. The organic solvent was removed in vacuo and the pH of the aqueous residue was adjusted to 2 followd by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness and the residue was subjected to column chromatography eluting with 25% ethyl acetate/hexane to yield the title compound (0.09 g, 53%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 7.33 (dt, 1H), 7.14-7.03 (m, 2H), 6.93 (d, 1H), 6.66 (s, 1H), 6.06 (s, 1H), 5.88 (dd, 2H), 3.76-3.63 (m, 2H), 2.94 (q, 2H), 1.69-1.62 (m, 2H) 1.34-1.22 (m, 6H), 0.83 (t, 3H); 13C NMR (75 MHz, CDCl3) δ 175.9, 165.8, 148.3, 147.2, 144.6, 142.6, 129.9, 129.6, 123.8, 123.4, 114.7, 109.2, 105.1, 101.9, 99.8, 49.6, 40.3, 37.2, 31.2, 27.2, 26.4, 22.4, 13.9; MS (ES+) m/z 394.5 (M+1).

Workup

  1. customThe organic solvent was removed in vacuo
  2. extractionthe pH of the aqueous residue was adjusted to 2 followd by extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo to dryness
  6. washeluting with 25% ethyl acetate/hexane

Sources & evidence

ORD record
ord-2f8e215b688947e096820948cb8ff35c
Source dataset
uspto-grants-2010_04
Patent number
US07700641B2

Reaction notes

Loading…