3,5-Dichlorobenzaldehyde → N-(5-((1R,2S)-2-(3,5-Dichlorobenzylamino)-1-hydroxypropyl)-2-hydroxyphenyl)methanesulfonamide

HRID 218116Notes

Reaction equation

HRID 218116 reaction equation
[NH2:1][C@@H:2]([CH3:17])[C@@H:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:16])=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=1)[OH:4].[Cl:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([Cl:27])[CH:26]=1)[CH:22]=O>CO>[Cl:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([Cl:27])[CH:26]=1)[CH2:22][NH:1][C@@H:2]([CH3:17])[C@@H:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:16])=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=1)[OH:4]

Participants

4

Reactant 2

HCID 357463,5-DichlorobenzaldehydeHCID 58280635N-(5-((1R,2S)-2-Amino-1-hydroxypropyl)-2-hydroxyphenyl)methanesulfonamide

Product 1

HCID 44628409N-(5-((1R,2S)-2-(3,5-Dichlorobenzylamino)-1-hydroxypropyl)-2-hydroxyphenyl)methanesulfonamideYield 45.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Borane-pyridine complex (130 μL, 1.21 mmol) was added to an methanol solution (4 mL) of an amine (3) (105 mg, 0.40 mmol) and 3,5-dichlorobenzaldehyde (95 mg, 0.52 mmol) at 40° C. and the mixture was stirred for 1.5 hours. The reaction mixture was allowed to cool to room temperature and extracted after addition of water with a mixed solvent (ethyl acetate: methanol-10:1), and the organic layer was washed with saturated aqueous sodium chloride solution. The organic layer was dried and concentrated, and the crude product obtained was purified by amine silica gel column chromatography (eluant:chloroform:methanol=7:1), to give a desired amine (6) as a white solid (76 mg, yield 45%).

Workup

  1. extractionextracted
  2. additionafter addition of water with a mixed solvent (ethyl acetate: methanol-10:1)
  3. washthe organic layer was washed with saturated aqueous sodium chloride solution
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customthe crude product obtained
  7. customwas purified by amine silica gel column chromatography (eluant:chloroform:methanol=7:1)

Sources & evidence

ORD record
ord-e3b879a3c8494c3ca8d3a798a761c9df
Source dataset
uspto-grants-2012_06
Patent number
US08198330B2

Reaction notes

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