Water → N-(5-((1R,2S)-2-(3,5-Diethoxybenzylamino)-1-hydroxypropyl)-2-hydroxyphenyl)methanesulfonamide

HRID 1685901Notes

Reaction equation

HRID 1685901 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].[CH2:18]([O:20][C:21]1[CH:22]=[C:23]([CH:26]=[C:27]([O:29][CH2:30][CH3:31])[CH:28]=1)[CH:24]=O)[CH3:19].O>CO>[CH2:30]([O:29][C:27]1[CH:26]=[C:23]([CH:22]=[C:21]([O:20][CH2:18][CH3:19])[CH:28]=1)[CH2:24][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])[CH3:31]

Participants

5

Reactant 3

HCID 962WaterHCID 226086163,5-DiethoxybenzaldehydeHCID 58280635N-(5-((1R,2S)-2-Amino-1-hydroxypropyl)-2-hydroxyphenyl)methanesulfonamide

Product 1

HCID 44628485N-(5-((1R,2S)-2-(3,5-Diethoxybenzylamino)-1-hydroxypropyl)-2-hydroxyphenyl)methanesulfonamideYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the amine (4) (127 mg, 0.486 mmol) and 3,5-diethoxybenzaldehyde (123 mg, 0.632 mmol) in methanol (3.3 mL) was added borane-pyridine complex (155 μL, 1.46 mmol) at 40° C. and the resulting mixture was stirred for 2.5 hours. The reaction mixture was cooled to room temperature and water was added thereto, followed by extraction with a mixed solvent (ethyl acetate:methanol=10:1) and subsequent washing of the organic layer with saturated brine. The organic layer was dried and concentrated and the obtained crude product was purified by amine silica gel column chromatography (eluent; chloroform:methanol=7:1) to obtain the desired amine (10) as a yellow solid (114 mg, Yield: 54%).

Workup

  1. extractionfollowed by extraction with a mixed solvent (ethyl acetate:methanol=10:1)
  2. washsubsequent washing of the organic layer with saturated brine
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customthe obtained crude product
  6. customwas purified by amine silica gel column chromatography (eluent; chloroform:methanol=7:1)

Sources & evidence

ORD record
ord-37681f8db363493fa000152b49f16b80
Source dataset
uspto-grants-2012_04
Patent number
US08148427B2

Reaction notes

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