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

HRID 218119ノート

反応式

HRID 218119 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].[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]>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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Borane-pyridine complex (155 μL, 1.46 mmol) was added to a methanol solution (3.3 mL) of an amine (3) (127 mg, 0.486 mmol) and 3,5-diethoxybenzaldehyde (123 mg, 0.632 mmol) at 40° C. and the mixture was stirred for 2.5 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 (9) as a yellow solid (114 mg, yield 54%).

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-92cea96138b146f090126778c310d877
出典データセット
uspto-grants-2012_06
特許番号
US08198330B2

反応ノート

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