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

HRID 218119노트

반응식

HRID 218119 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-92cea96138b146f090126778c310d877
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198330B2

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