Water → 5-(4-Chloro-phenyl)-N-((R)-1-hydroxymethyl-3-methyl-butyl)-6-(2-propionylamino-ethoxy)-nicotinamide

HRID 1929833Notes

Reaction equation

HRID 1929833 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([O:27][CH2:28][CH2:29][NH:30][C:31](=[O:34])[CH2:32][CH3:33])=[N:10][CH:11]=[C:12]([C:14]([N:16]3[C@H:20]([CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:19][O:18]C3(C)C)=[O:15])[CH:13]=2)=[CH:4][CH:3]=1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.O.C(=O)(O)[O-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([O:27][CH2:28][CH2:29][NH:30][C:31](=[O:34])[CH2:32][CH3:33])=[N:10][CH:11]=[C:12]([CH:13]=2)[C:14]([NH:16][C@@H:20]([CH2:19][OH:18])[CH2:21][CH:22]([CH3:24])[CH3:23])=[O:15])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 516892Sodium BicarbonateHCID 67505397N-{2-[3-(4-Chloro-phenyl)-5-((R)-4-isobutyl-2,2-dimethyl-oxazolidine-3-carbonyl)-pyridin-2-yloxy]-ethyl}-propionamide

Product 1

HCID 248572515-(4-Chloro-phenyl)-N-((R)-1-hydroxymethyl-3-methyl-butyl)-6-(2-propionylamino-ethoxy)-nicotinamideYield 76.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-{2-[3-(4-Chloro-phenyl)-5-((R)-4-isobutyl-2,2-dimethyl-oxazolidine-3-carbonyl)-pyridin-2-yloxy]-ethyl}-propionamide (82 mg, 0.16 mmol) was dissolved in methanol (0.35 mL). To the solution was added camphorsulfonic acid (1.6 mg, 0.007 mmol) and the reaction mixture was stirred for 1 h at RT. The mixture was poured into water, sodiumbicarbonate was added and the mixture extracted with ethyl acetate. Organic phases were pooled, the solvent was evaporated in vacuo and the residue was purified by column chromatography on silica (dichloromethane/methanol gradient) to yield 55 mg of the title compound as a white solid, MS (ISP) 448.3 (M+H)+.

Workup

  1. additionwas added
  2. extractionthe mixture extracted with ethyl acetate
  3. customthe solvent was evaporated in vacuo
  4. customthe residue was purified by column chromatography on silica (dichloromethane/methanol gradient)

Sources & evidence

ORD record
ord-c59670a0c4ad4760aa184c64df80061f
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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