Lithium Hydroxide → HCID 59599512, compound

HRID 2267025Notes

Reaction equation

HRID 2267025 reaction equation
C[O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][C:11]2[CH:12]=[N:13][CH:14]=[C:15]([CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([C:25](=[O:27])[CH3:26])=[C:21]([OH:28])[C:20]=3[CH2:29][CH2:30][CH3:31])[CH:16]=2)[CH:5]=1.[OH-].[Li+]>CO.O>[C:25]([C:22]1[CH:23]=[CH:24][C:19]([O:18][CH2:17][C:15]2[CH:16]=[C:11]([S:10][C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:32])=[O:2])[CH:12]=[N:13][CH:14]=2)=[C:20]([CH2:29][CH2:30][CH3:31])[C:21]=1[OH:28])(=[O:27])[CH3:26]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68537777HCID 68537777, compound

Product 1

HCID 59599512HCID 59599512, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Dissolve 3-[5-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-pyridin-3-ylsulfanyl]-benzoic acid methyl ester (379 mg, 0.84 mmol) in methanol (2 mL) and water (0.5 mL). Add 2N aqueous lithium hydroxide solution (0.42 mL, 0.84 mmol). After 12 hours, concentrate under reduced pressure and dissolve residue in 4N hydrochloric acid in dioxane. Add water until white precipitate forms, and collect by filtration. Triturate in ethyl acetate, then methanol. Collect the title compound by filtration as a white solid (317 mg, 0.73 mmol): 1H NMR (DMSO-d6) δ 0.76 (t, 3H), 1.37 (m, 2H), 2.47 (m, 2H), 2.58 (s, 3H), 5.30 (s, 2H), 6.70 (d, 1H), 7.52 (t, 1H), 7.63 (m, 1H), 7.77 (m, 1H), 7.80 (m, 1H), 7.86 (m, 1H), 7.90 (d, 1H), 8.60 (m, 2H), 12.83 (s, 1H), 13.21 (br s, 1H); MS (m/z): 438 (M+1).

Workup

  1. concentrationconcentrate under reduced pressure
  2. dissolutiondissolve residue in 4N hydrochloric acid in dioxane
  3. filtrationAdd water until white precipitate forms, and collect by filtration
  4. customTriturate in ethyl acetate
  5. customCollect the title compound

Sources & evidence

ORD record
ord-305fad881b0d4921b211eb2e6f88fe7d
Source dataset
uspto-grants-2010_12
Patent number
US07858646B2

Reaction notes

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