Triethylamine → N,N'-bis[(1S)-(1-naphthyl)-2-hydroxy-2-methylpropyl]-2,2-dimethylpropane-1,3-diamide

HRID 1182404

반응식

HRID 1182404 반응식
[NH2:1][C@@H:2]([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1)[C:3]([CH3:6])([OH:5])[CH3:4].C([N:19]([CH2:22][CH3:23])CC)C.[CH3:24][C:25]([CH3:32])([C:29](Cl)=[O:30])[C:26](Cl)=[O:27].[Cl-].[NH4+]>ClCCl>[C:7]1([C@H:2]([NH:1][C:26](=[O:27])[C:25]([CH3:32])([CH3:24])[C:29]([NH:19][C@@H:22]([C:23]2[C:10]3[C:11](=[CH:16][CH:7]=[CH:8][CH:9]=3)[CH:12]=[CH:13][CH:14]=2)[C:3]([CH3:4])([OH:5])[CH3:2])=[O:30])[C:3]([OH:5])([CH3:6])[CH3:4])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 4523180Dimethylmalonyl DichlorideHCID 11961966(S)-1-amino-1-(1-naphthyl)-2-methyl-2-propanol

생성물 1

HCID 66808051N,N'-bis[(1S)-(1-naphthyl)-2-hydroxy-2-methylpropyl]-2,2-dimethylpropane-1,3-diamide수율 102.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-10 °C

실험 절차

Under a nitrogen atmosphere, 2 g of (S)-1-amino-1-(1-naphthyl)-2-methyl-2-propanol, 1.1 g of triethylamine (dehydrated), and 17 mL of dichloromethane (dehydrated) were mixed and then cooled to an inner temperature of −10° C. 0.8 g of dimethylmalonic acid dichloride was added dropwise thereto over 3 minutes and the resulting mixture was warmed to room temperature. The mixture was stirred as such for 6 hours to effect reaction. After completion of the reaction, 20 mL of an aqueous saturated ammonium chloride solution was added thereto to separate into layers. The organic layer obtained was washed three times with 25 mL of water and concentrated. The concentrated residue was dried. under reduced pressure at an inner temperature of 40° C. to obtain 2.5 g of N,N′-bis[(1S)-(1-naphthyl)-2-hydroxy-2-methylpropyl]-2,2-dimethylpropane-1,3-diamide (yield: 100%).

후처리

  1. temperaturethe resulting mixture was warmed to room temperature
  2. customreaction
  3. additionwas added
  4. customto separate into layers
  5. customThe organic layer obtained
  6. washwas washed three times with 25 mL of water
  7. concentrationconcentrated
  8. customThe concentrated residue was dried

출처 및 근거

ORD 기록
ord-55597bd269214294a9ddb85063280212
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07288674B2

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