Lithium Hydroxide → HCID 11620001, compound

HRID 2244024Notes

Reaction equation

HRID 2244024 reaction equation
C[O:2][C:3](=[O:35])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([C:28](=[O:30])[CH3:29])=[C:24]([OH:31])[C:23]=3[CH2:32][CH2:33][CH3:34])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:6][CH:5]=1.[OH-].[Li+]>CO>[C:28]([C:25]1[CH:26]=[CH:27][C:22]([O:21][CH2:20][C:17]2[CH:18]=[CH:19][C:14]([S:11]([NH:10][C:7]3[CH:8]=[CH:9][C:4]([C:3]([OH:35])=[O:2])=[CH:5][CH:6]=3)(=[O:13])=[O:12])=[CH:15][CH:16]=2)=[C:23]([CH2:32][CH2:33][CH3:34])[C:24]=1[OH:31])(=[O:30])[CH3:29]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59212589HCID 59212589, compound

Product 1

HCID 11620001HCID 11620001, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve 4-[4-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-benzenesulfonylamino]-benzoic acid methyl ester (1.48 g, 2.98 mmol) in methanol (15 mL) and add 2N aqueous lithium hydroxide solution (9 mL). Stir 24 hours. Concentrate under reduced pressure to remove majority of methanol, add 1N hydrochloric acid to the dark brown solution to afford a white precipitate. Triturate in 1N hydrochloric acid for 1 hour and collect the solid by filtration. Triturate the collected solid in 1:1 ether/hex and filter to collect the title compound as a white solid (1.102 g, 2.28 mmol): 1H NMR (DMSO-d6) δ 0.85 (t, 3H), 1.46 (m, 2H), 2.58 (m, 5H), 5.30 (s, 2H), 6.65 (d, 1H), 7.20 (d, 2H), 7.61 (d, 2H), 7.80 (m, 3H), 7.87 (m, 2H), 10.82 (br s, 1H), 12.72 (br s, 1H), 12.82 (s, 1H); MS (m/z): 482 (M−1).

Workup

  1. concentrationConcentrate under reduced pressure
  2. customto remove majority of methanol
  3. additionadd 1N hydrochloric acid to the dark brown solution
  4. customto afford a white precipitate
  5. customTriturate in 1N hydrochloric acid for 1 hour
  6. customcollect the solid
  7. filtrationby filtration
  8. customTriturate the collected solid in 1:1 ether/hex
  9. filtrationfilter

Sources & evidence

ORD record
ord-a4c7e3b89b7340e49020c517fa132825
Source dataset
uspto-grants-2010_03
Patent number
US07678794B2

Reaction notes

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