Lithium hydroxide, monohydrate → (5-{3-[4-(4-ethyl-1,3-thiazol-2-yl)-2-propylphenoxy]propoxy}-1H-indol-1-yl)acetic acid

HRID 2424964Notes

Reaction equation

HRID 2424964 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH2:15][CH2:16][CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]4[S:26][CH:27]=[C:28]([CH2:30][CH3:31])[N:29]=4)=[CH:21][C:20]=3[CH2:32][CH2:33][CH3:34])=[CH:11][CH:12]=2)[CH:7]=[CH:6]1.O[Li].O>C1COCC1.O>[CH2:30]([C:28]1[N:29]=[C:25]([C:22]2[CH:23]=[CH:24][C:19]([O:18][CH2:17][CH2:16][CH2:15][O:14][C:10]3[CH:9]=[C:8]4[C:13](=[CH:12][CH:11]=3)[N:5]([CH2:4][C:3]([OH:35])=[O:2])[CH:6]=[CH:7]4)=[C:20]([CH2:32][CH2:33][CH3:34])[CH:21]=2)[S:26][CH:27]=1)[CH3:31]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 57845429methyl(5-{3-[4-(4-ethyl-1,3-thiazol-2-yl)-2-propylphenoxy]propoxy}-1H-indol-1-yl)acetate

Product 1

HCID 11282992(5-{3-[4-(4-ethyl-1,3-thiazol-2-yl)-2-propylphenoxy]propoxy}-1H-indol-1-yl)acetic acidYield 75.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl(5-{3-[4-(4-ethyl-1,3-thiazol-2-yl)-2-propylphenoxy]propoxy}-1H-indol-1-yl)acetate (Example 53, 89 mg, 0.18 mmol) in 3.0 mL THF, was added LiOH.H2O (30 mg, 0.72 mmol) in water (1.0 mL). The mixture was stirred for 12 h at rt. The solvents were evaporated and the residue was suspended in a small volume of water. The pH of the mixture was adjusted to 3 with 1 N HCl. The aqueous layer was extracted with ethyl acetate. The combined organic layers were concentrated to give 65 mg (75%) of the product as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.42 (d, 1H), 7.35 (dd, 1H), 7.10-7.05 (m, 2H), 7.08 (d, 1H), 6.90 (dd, 1H), 6.78 (s, 1H), 6.45 (d, 1H), 6.35 (d, 1H), 4.85 (s, 2H), 4.34 (t, 2H), 4.26 (t, 2H), 2.92 (q, 2H), 2.55-2.45 (m, 2H), 2.25-2.15 (m, 2H), 1.62-1.50 (m, 2H), 1.35 (t, 3H), 0.92 (t, 3H).

Workup

  1. customThe solvents were evaporated
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. concentrationThe combined organic layers were concentrated

Sources & evidence

ORD record
ord-61e21e3b8b6f485ca9440ee46c41852f
Source dataset
uspto-grants-2011_06
Patent number
US07964622B2

Reaction notes

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