Water → OPC 51803

HRID 1870260ノート

反応式

HRID 1870260 の反応式
[C:1]([CH2:4][C@@H:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]([C:16](=[O:29])[C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:19][C:18]=2[Cl:28])[CH2:8][CH2:7][CH2:6]1)([OH:3])=O.[CH:30]([NH2:33])([CH3:32])[CH3:31].P(C#N)(OCC)(OCC)=O.O>CN(C)C=O.C(OCC)(=O)C.CCCCCC>[CH:30]([NH:33][C:1]([CH2:4][C@@H:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]([C:16](=[O:29])[C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:19][C:18]=2[Cl:28])[CH2:8][CH2:7][CH2:6]1)=[O:3])([CH3:32])[CH3:31]

参加物

7

反応物 4

HCID 962WaterHCID 6363IsopropylamineHCID 76257Diethyl cyanophosphonateHCID 11058732HCID 11058732、化合物

生成物 1

HCID 3038506OPC 51803

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 21226206Ethyl acetate hexane溶媒

実験手順

To a solution of (5R)-5-carboxymethyl-1-[4-(1-pyrrolidinyl)-2-chlorobenzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (21 g) in dimethylformamide (400 ml) are added isopropylamine (21.7 ml) and diethyl cyanophosphate (10 g) at room temperature, and the mixture is stirred at room temperature for two hours. To the reaction solution are added water and ethyl acetate--n-hexane (10:1), and the mixture is extracted twice. The organic layer is washed successively with a 5% citric acid, a saturated aqueous sodium hydrogen carbonate solution, and water, and dried over anhydrous magnesium sulfate. The mixture is concentrated under reduced pressure to remove the solvent, and the resulting residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol:ammonium hydroxide=1000:5:0.2→1000:15:0.5), and recrystallized from acetone--n-hexane to give (5R)-5-isopropylaminocarbonylmethyl-1-[4-(1-pyrrolidinyl)-2-chlorobenzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (12.5 g).

後処理

  1. extractionthe mixture is extracted twice
  2. washThe organic layer is washed successively with a 5% citric acid
  3. dry with materiala saturated aqueous sodium hydrogen carbonate solution, and water, and dried over anhydrous magnesium sulfate
  4. concentrationThe mixture is concentrated under reduced pressure
  5. customto remove the solvent
  6. customthe resulting residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol:ammonium hydroxide=1000:5:0.2→1000:15:0.5)
  7. customrecrystallized from acetone

出典と根拠

ORDレコード
ord-2010a8ad820f4c61a580c4af3ad99e67
出典データセット
uspto-grants-2000_08
特許番号
US06096736

反応ノート

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