Acetic Acid → HCID 9829796, compound

HRID 843689Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)=[CH:21][CH:20]=1)[C:13]([C:34]1[CH:39]=[CH:38][C:37]([O:40]C(=O)C(C)(C)C)=[CH:36][CH:35]=1)=[C:12]2[CH3:47])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[Li].O.CC(O)=O.O>O1CCOCC1.CO.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:28]3[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]3)=[CH:21][CH:20]=1)[C:13]([C:34]1[CH:35]=[CH:36][C:37]([OH:40])=[CH:38][CH:39]=1)=[C:12]2[CH3:47])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of the substituted indole 23 (61.8 g, 0.098 mol, 1 eq) and LiOH.H2O (8.5 g, 0.202 mol, 2.1 eq) in dioxane/MeOH/H2O (300 mL, 150 mL, 150 mL) was stirred at 60° C. for 2 h. The mixture was cooled to rt and 12.1 mL of AcOH was added in order to adjust the pH to approximately 7. Then water (600 mL) was added and the mixture was extracted with CH2Cl2 (6×150 mL), the organic phase was washed with conc. Aq. Na2CO3, H2O, brine, dried over Na2SO4, and evaporated to give 31 (51.6 g, 97%) as a yellow foam: 1H NMR (CDCl3) δ 7.07 (m, 19 H), 6.10 (s, 2 H), 5.03 (s, 2 H), 4.03 (t, 2 H), 2.8 (t, 2 H), 2.53 (br s, 4 H), 2.21 (s, 3 H), 1.63 (t, 4 H), 1.43 (br s, 2 H).

Workup

temperatureThe mixture was cooled to rt
extractionthe mixture was extracted with CH2Cl2 (6×150 mL)
washthe organic phase was washed with conc. Aq. Na2CO3, H2O, brine
dry with materialdried over Na2SO4
customevaporated

Sources & evidence

ORD record: ord-648be7ea20474d938b00db70df5ed352
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06380166B1

Reaction notes

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