Propanal → Methyl 3-[4-({3-[[(4-phenyl-1,3-thiazol-2-yl)methyl](propyl)amino]benzyl}oxy)phenyl]propanoate

HRID 732191ノート

反応式

HRID 732191 の反応式
[C:1]1([C:7]2[N:8]=[C:9]([CH:12]=O)[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:14][C:15]1[CH:16]=[C:17]([CH:32]=[CH:33][CH:34]=1)[CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])=[CH:22][CH:21]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH:49](=O)[CH2:50][CH3:51]>O.ClCCCl.C(O)(=O)C>[C:1]1([C:7]2[N:8]=[C:9]([CH2:12][N:14]([CH2:49][CH2:50][CH3:51])[C:15]3[CH:16]=[C:17]([CH:32]=[CH:33][CH:34]=3)[CH2:18][O:19][C:20]3[CH:21]=[CH:22][C:23]([CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])=[CH:24][CH:25]=3)[S:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

8

反応物 4

HCID 527PropanalHCID 35388144-Phenyl-1,3-thiazole-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 23143302Methyl 3-{4-[(3-aminobenzyl)oxy]phenyl}-propanoate

生成物 1

HCID 23143254Methyl 3-[4-({3-[[(4-phenyl-1,3-thiazol-2-yl)methyl](propyl)amino]benzyl}oxy)phenyl]propanoate収率 78.5%

試薬・触媒・溶媒 3

HCID 111,2-Dichloroethane溶媒HCID 176Acetic Acid溶媒HCID 962Water溶媒

実験手順

To a mixture of 4-phenyl-1,3-thiazole-2-carbaldehyde (210 mg, 1.1 mmol), methyl 3-{4-[(3-aminobenzyl)oxy]phenyl}-propanoate (285 mg, 1.0 mmol), acetic acid (0.2 mL) and 1,2-dichloroethane (5 mL) was added sodium triacetoxyborohydride (0.6 g, 2.8 mmol) under ice-cooling, and the mixture was warmed to room temperature and stirred for 1 hr. Propanal (200 mg, 3.4 mmol) was added to the reaction mixture, and the mixture was further stirred at room temperature for 1 hr. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19-1:2 in volume ratio) to give the title compound (393 mg, yield 78%) as a yellow oil.

後処理

  1. temperaturecooling
  2. stirringthe mixture was further stirred at room temperature for 1 hr
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19-1:2 in volume ratio)

出典と根拠

ORDレコード
ord-fcf9313ff1bb41baac2c41f165c80b30
出典データセット
uspto-grants-2009_09
特許番号
US07585880B2

反応ノート

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