Methanol → HCID 10177620, compound

HRID 1072686Notes

Reaction equation

HRID 1072686 reaction equation
[CH3:1][CH:2]([O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=[O:23])=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)[CH2:3][NH:4][S:5]([CH:8]([CH3:10])[CH3:9])(=[O:7])=[O:6].[OH-].[Li+].C1COCC1.CO>O>[CH3:1][CH:2]([O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[CH:20][C:21]([C:22]([OH:24])=[O:23])=[CH:26][CH:27]=2)=[CH:14][CH:13]=1)[CH2:3][NH:4][S:5]([CH:8]([CH3:9])[CH3:10])(=[O:7])=[O:6]

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 10293862HCID 10293862, compound

Product 1

HCID 10177620HCID 10177620, compoundYield 292.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 4-[4-(1-methyl-2-{[(methylethyl)sulfonyl]amino}ethoxy)phenyl]benzoate (30 mg, 0.077 mmol), lithium hydroxide (11 mg, 0.268 mmol), THF (1.2 mL), methanol (0.4 mL) and deionized water (0.4 mL) were combined in a 15 mL round bottomed flask and stirred at room temperature overnight. The reaction mixture was concentrated in-vacuo, and dissolved in 1 N sodium hydroxide. This solution was acidified (pH=2) with 1 N hydrochloric acid, and was extracted three times with methylene chloride. The organic extractions were combined, washed with 15 mL water, dried with magnesium sulfate, filtered, and concentrated in-vacuo, yielding 85 mg of yellow solid. This material was further purified using a 1000 uM rotor on a Chromatotron in a 1:1 methylene chloride:ethyl acetate solvent system to provide the title compound (65 mg, 100%) as waxy brown paste.

Workup

  1. concentrationThe reaction mixture was concentrated in-vacuo
  2. dissolutiondissolved in 1 N sodium hydroxide
  3. extractionwas extracted three times with methylene chloride
  4. extractionThe organic extractions
  5. washwashed with 15 mL water
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-6aba6f322f444e2da3f6007db84c1a8b
Source dataset
uspto-grants-2005_06
Patent number
US06911476B2

Reaction notes

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