Water → OPC 51803

HRID 1870260노트

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HRID 1870260 반응식
[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]

참가 물질

7

반응물 4

HCID 962WaterHCID 6363IsopropylamineHCID 76257Diethyl cyanophosphonateHCID 11058732HCID 11058732, 화합물

생성물 1

HCID 3038506OPC 51803

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 21226206Ethyl acetate hexane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2010a8ad820f4c61a580c4af3ad99e67
출처 데이터셋
uspto-grants-2000_08
특허 번호
US06096736

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