Lithium Hydroxide → HCID 59263366, compound

HRID 425725Notes

Reaction equation

HRID 425725 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 followed 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. extractionfollowed 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-7196056f9482443fb27b4ff79f9e8eff
Source dataset
uspto-grants-2012_01
Patent number
US08106087B2

Reaction notes

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