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

HRID 1685900

反応式

HRID 1685900 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.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

5

反応物 3

HCID 962WaterHCID 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

To a solution of the amine (4) (131 mg, 0.50 mmol) and 3,5-dimethylbenzaldehyde (90 μL, 0.65 mmol) in methanol (5 mL) was added borane-pyridine complex (160 μL, 1.50 mmol) at 40° C. and the resulting mixture was stirred for 1.5 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 (9) as a white solid (62 mg, Yield: 33%).

後処理

  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)

出典と根拠

ORDレコード
ord-0329ab4d23a24d03aa862619fca0e448
出典データセット
uspto-grants-2012_04
特許番号
US08148427B2

関連ノート

読み込み中…