Lithium hydroxide, monohydrate → 4-{[4-(4-Butyl-phenylethynyl)-benzyl]-hexyl-amino}-2-hydroxy-benzoic acid

HRID 551930Notes

Reaction equation

HRID 551930 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:39]=[CH:38][C:16]([CH2:17][N:18]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[C:19]3[CH:20]=[CH:21][C:22]4[C:27](=[O:28])[O:26]C(C)(C)[O:24][C:23]=4[CH:31]=3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].O.[OH-].[Li+]>C1COCC1.O.CCOCC>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:39]=[CH:38][C:16]([CH2:17][N:18]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[C:19]3[CH:20]=[CH:21][C:22]([C:27]([OH:28])=[O:26])=[C:23]([OH:24])[CH:31]=3)=[CH:15][CH:14]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 115409437-[{4-[(4-butylphenyl)ethynyl]benzyl}(hexyl)amino]-2,2-dimethyl-4H-1,3-benzodioxin-4-one

Product 1

HCID 116071814-{[4-(4-Butyl-phenylethynyl)-benzyl]-hexyl-amino}-2-hydroxy-benzoic acidYield 78%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-[{4-[(4-butylphenyl)ethynyl]benzyl}(hexyl)amino]-2,2-dimethyl-4H-1,3-benzodioxin-4-one (613 mg, 1.2 mmol) in THF (18 mL) was added a suspension of lithium hydroxide monohydrate (1.47 g, 35.1 mmol) in water (5.0 mL). The resulting mixture was refluxed for 48 hrs. The reaction mixture was diluted with Et2O (60 mL) and washed with an aqueous solution of HCl (3×15 mL, 1N) and brine. The organic layer was dried over MgSO4 and the solvents were removed under reduced pressure to give 443 mg (78%) of the title compound as a yellow powder. HPLC, Rt: 6.2 min (purity: 97.7%). LC/MS, M−(ESI): 482.2. 1H NMR (CDCl3) δ: 10.59 (s, 1H), 7.66 (d, J=9 Hz, 1H), 7.45 (m, 4H), 7.13 (m, 4H), 6.21 (m, 1H), 6.14 (m, 1H), 4.58 (s, 2H), 3.40 (m, 2H), 2.60 (t, J=7.5 Hz, 2H), 1.72-1.51 (m, 2H), 1.42-1.20 (m, 10H), 0.95-0.82 (m, 6H).

Workup

  1. temperatureThe resulting mixture was refluxed for 48 hrs
  2. washwashed with an aqueous solution of HCl (3×15 mL, 1N) and brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-d6cb5e5e4b7940f0b53f2c77155ad155
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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