Lithium Hydroxide → HCID 57845354, compound

HRID 734426Notes

Reaction equation

HRID 734426 reaction equation
C[O:2][C:3](=[O:35])[CH:4]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]4[O:27][CH:28]=[C:29]([CH2:31][CH3:32])[N:30]=4)=[CH:22][C:21]=3[O:33][CH3:34])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)[CH3:5].[OH-].[Li+]>O1CCCC1.CO.O>[CH2:31]([C:29]1[N:30]=[C:26]([C:23]2[CH:24]=[CH:25][C:20]([O:19][CH2:18][CH2:17][CH2:16][O:15][C:11]3[CH:10]=[C:9]4[C:14](=[CH:13][CH:12]=3)[N:6]([CH:4]([CH3:5])[C:3]([OH:35])=[O:2])[CH:7]=[CH:8]4)=[C:21]([O:33][CH3:34])[CH:22]=2)[O:27][CH:28]=1)[CH3:32]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 57845457HCID 57845457, compound

Product 1

HCID 57845354HCID 57845354, compoundYield 79.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(5-{3-[4-(4-Ethyl-oxazol-2-yl)-2-methoxy-phenoxy]-propoxy}-indol-1-yl)-propionic acid methyl ester (Example 62, 129.7 mg, 0.27 mmol) was dissolved in a solution of tetrahydrofuran (2 mL), methanol (1 mL), and water (2 mL). Lithium hydroxide (32.45 mg, 1.36 mmol) was added and the mixture was stirred at rt for 2 h. The solution was concentrated, diluted with water (5 mL), and acidified with 1N HCl. The resulting white precipitate was collected by filtration and dried to give the title compound (100.1 mg, 79.5%). LC/MS m/z 465.1 (M+H)+; RT 3.25 min. 1H NMR (400 MHz, DMSO-d6) δ 7.82 (s, 1H), 7.47 (dd, 1H), 7.42 (d, 1H), 7.37 (d, 1H), 7.28 (d, 1H), 7.11 (d, 1H), 7.06 (d, 1H), 6.77 (dd, 1H), 6.34 (d, 1H), 5.24 (q, 1H), 4.19 (t, 2H), 4.12 (t, 2H), 3.82 (s, 3H), 2.52 (m, 2H), 2.20 (m, 2H), 1.68 (d, 3H), 1.19 (t, 3H).

Workup

  1. concentrationThe solution was concentrated
  2. additiondiluted with water (5 mL)
  3. filtrationThe resulting white precipitate was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-6e889f00840e4010b0ae6471130d695f
Source dataset
uspto-grants-2009_09
Patent number
US07592361B2

Reaction notes

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