3,5-Dichlorobenzaldehyde → HCID 44628409, 화합물

HRID 218116

반응식

HRID 218116 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].[Cl:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([Cl:27])[CH:26]=1)[CH:22]=O>CO>[Cl:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([Cl:27])[CH:26]=1)[CH2:22][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]

참가 물질

4

반응물 2

HCID 357463,5-DichlorobenzaldehydeHCID 58280635N-(5-((1R,2S)-2-Amino-1-hydroxypropyl)-2-hydroxyphenyl)methanesulfonamide

생성물 1

HCID 44628409HCID 44628409, 화합물수율 45.3%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Borane-pyridine complex (130 μL, 1.21 mmol) was added to an methanol solution (4 mL) of an amine (3) (105 mg, 0.40 mmol) and 3,5-dichlorobenzaldehyde (95 mg, 0.52 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 (6) as a white solid (76 mg, yield 45%).

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-e3b879a3c8494c3ca8d3a798a761c9df
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198330B2

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