Benzaldehyde, 3,5-dimethyl- → N-(5-((1R,2S)-2-(3,5-Dimethylbenzylamino)-1-hydroxypropyl)-2-hydroxyphenyl)methanesulfonamide

HRID 218118

反応式

HRID 218118 の反応式
[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].[CH3:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([CH3:27])[CH:26]=1)[CH:22]=O>CO>[CH3:18][C:19]1[CH:26]=[C:25]([CH:24]=[C:21]([CH3:22])[CH:20]=1)[CH2:27][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]

参加物

4

反応物 2

HCID 34225Benzaldehyde, 3,5-dimethyl-HCID 58280635N-(5-((1R,2S)-2-Amino-1-hydroxypropyl)-2-hydroxyphenyl)methanesulfonamide

生成物 1

HCID 44628484N-(5-((1R,2S)-2-(3,5-Dimethylbenzylamino)-1-hydroxypropyl)-2-hydroxyphenyl)methanesulfonamide収率 33%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Borane-pyridine complex (160 μL, 1.50 mmol) was added to a methanol solution (5 mL) of an amine (3) (131 mg, 0.50 mmol) and 3,5-dimethylbenzaldehyde (90 μL, 0.65 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 (8) as a white solid (62 mg, yield 33%).

後処理

  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)

出典と根拠

ORDレコード
ord-f6b63811fd6c4cf3b29ec7d1f9687130
出典データセット
uspto-grants-2012_06
特許番号
US08198330B2

関連ノート

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