Lithium hydroxide, monohydrate → HCID 57845373, compound

HRID 2424968Notes

Reaction equation

HRID 2424968 reaction equation
C[O:2][C:3](=[O:36])[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]([O:30][CH:31]([CH3:33])[CH3:32])[N:29]=4)=[CH:21][C:20]=3[O:34][CH3:35])=[CH:11][CH:12]=2)[CH:7]=[CH:6]1.O[Li].O>C1COCC1.O>[CH:31]([O: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:36])=[O:2])[CH:6]=[CH:7]4)=[C:20]([O:34][CH3:35])[CH:21]=2)[S:26][CH:27]=1)([CH3:32])[CH3:33]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 57845510HCID 57845510, compound

Product 1

HCID 57845373HCID 57845373, compoundYield 91.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl(5-{3-[4-(4-isopropoxy-1,3-thiazol-2-yl)-2-methoxyphenoxy]propoxy}-1H-indol-1-yl)acetate (Example 56, 204 mg, 0.40 mmol) was dissolved in THF (3 mL) in a round bottom flask, and LiOH.H2O (67 mg, 1.60 mmol) in water (1 mL) was added. The mixture was stirred at rt for 16 h. The solvents were evaporated under reduced pressure and the residue was suspended in small volume of water. The pH of the mixture was adjusted to 3 with 1 N HCl. The aqueous layer was immediately extracted with EtOAc. The combined organic layers were dried, filtered, and concentrated to give 182 mg (91%) of the product as a white solid. 1H NMR (400 MHz, CDCl3) δ: 7.42 (s, 1H), 7.32 (d, 1H), 7.15-7.08 (m, 2H), 7.04 (d, 1H), 6.88 (dd, 1H), 6.82 (d, 1H), 6.52 (d, 1H), 5.96 (s, 1H), 4.85 (s, 2H), 4.70-4.60 (q, 1H), 4.35-4.20 (m, 4H), 3.88 (s, 3H), 2.38-2.28 (m, 2H), 1.42 (d, 6H).

Workup

  1. customThe solvents were evaporated under reduced pressure
  2. extractionThe aqueous layer was immediately extracted with EtOAc
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-20f32d9c41814ec7a2e66c410ae205a9
Source dataset
uspto-grants-2011_06
Patent number
US07964622B2

Reaction notes

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