Potassium Carbonate → N-[4-[4-[Ethyl(5-hydroxy-5-methylhexyl)amino]-1-hydroxybutyl]phenyl]methanesulfonamide

HRID 1654308Notes

Reaction equation

HRID 1654308 reaction equation
[CH2:1]([N:3]([CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:27]C(=O)C)([CH3:26])[CH3:25])[CH2:4][CH2:5][CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])=[CH:11][CH:10]=1)[OH:8])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO.O>[CH2:1]([N:3]([CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:27])([CH3:26])[CH3:25])[CH2:4][CH2:5][CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][S:16]([CH3:19])(=[O:17])=[O:18])=[CH:11][CH:10]=1)[OH:8])[CH3:2]

Participants

5

Reactant 2

HCID 11430Potassium Carbonate2×HCID 15294461N-(4-(4-(Ethyl(5-acetoxy-5-methylhexyl)amino)-1-hydroxybutyl)phenyl)methanesulfonamide

Product 1

HCID 15294462N-[4-[4-[Ethyl(5-hydroxy-5-methylhexyl)amino]-1-hydroxybutyl]phenyl]methanesulfonamideYield 35.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A stirred mixture of the product from Example 25 (0.92 g, 2.08 mmol) and 17.2 mL of a solution of potassium carbonate (5 g) in MeOH (80 mL) and water (20 mL) was refluxed, under nitrogen for 24 h. An additional 17.2 mL of the potassium carbonate solution was added and reflux was continued for 24 h. The mixture was then concentrated to remove MeOH and the aqueous residue was adjusted to pH 8 and washed with EtOAc. The aqueous solution was then concentrated to dryness, and the solid residue was extracted with CH2Cl2. This extract was concentrated and the residue was chromatographed on silica gel with 10% MeOH--1% NH4OH-CHCl3 to give 0.292 g (35.1%) of the titled product, a compound of Formula I': NMR (CDCl3) δ1.09 (t, 3H), 1.21 (s, 6H), 1.53 (m, 9H), 1.97 (m, 1H), 2.55 (m, 6H), 2.94 (s, 3H), 4.61 (m, 1H), 7.15 (d, 2H), 7.35 (d, 2H); MS m/z (relative intensity) 400 (M+, 17.4), 385 (14.5), 367 (11.1), 321 (36.6), 299 (92.8), 172 (100).

Workup

  1. temperaturewas refluxed, under nitrogen for 24 h
  2. temperaturereflux
  3. concentrationThe mixture was then concentrated
  4. customto remove MeOH
  5. washwashed with EtOAc
  6. concentrationThe aqueous solution was then concentrated to dryness
  7. extractionthe solid residue was extracted with CH2Cl2
  8. concentrationThis extract was concentrated
  9. customthe residue was chromatographed on silica gel with 10% MeOH--1% NH4OH-CHCl3

Sources & evidence

ORD record
ord-b503430a5fdd4667860bfb288afb07e2
Source dataset
uspto-grants-1995_04
Patent number
US05405997

Reaction notes

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