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

HRID 508042
ノート
印刷プレビュー

反応式

HRID 508042 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]([CH2:26][C:27]1[CH:32]=[CH:31][C:30](/[N:33]=[CH:34]/[C:35]2[S:36][CH:37]=[C:38]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[N:39]=2)=[CH:29][CH:28]=1)[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:16][CH:15]=1)(=[O:12])=[O:11])([O-:3])=[O:2].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH:60](=O)[CH2:61][CH3:62].C(=O)([O-])O.[Na+]>ClCCCl>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]([CH2:34][C:35]2[S:36][CH:37]=[C:38]([C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[N:39]=2)[CH2:60][CH2:61][CH3:62])=[CH:29][CH:28]=1)[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:16][CH:15]=1)(=[O:12])=[O:11])([O-:3])=[O:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 527PropanalHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 178499916HCID 178499916、化合物

生成物 1

HCID 23157528Methyl 3-[4-([(2-nitrophenyl)sulfonyl]{4-[[(4-phenyl-1,3-thiazol-2-yl)methyl](propyl)amino]benzyl}amino)phenyl]propanoate収率 80%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

The yellow oil obtained in Example 50 was dissolved in 1,2-dichloroethane (20 mL), sodium triacetoxyborohydride (1.26 g, 6.0 mmol) was added at room temperature by small portions, and the mixture was stirred at room temperature for 60 hr. Propionaldehyde (200 mg, 3.0 mmol) was added to the reaction mixture at room temperature, and the mixture was stirred at room temperature for 3 hr. The reaction mixture was poured into 10% aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried using a Presep Dehydration tube (manufactured by Wako Pure Chemical Industries, Ltd.), and concentrated. The residue was purified by silica gel column chromatography (5%-70% ethyl acetate/hexane) to give the title compound (549 mg, yield 80%, 2 steps) as a yellow oil.

後処理

  1. stirringthe mixture was stirred at room temperature for 3 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe ethyl acetate layer was dried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (5%-70% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-05fb64052947452f94348111f83567b1
出典データセット
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07786165B2

反応ノート

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