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

HRID 1182404

反応式

HRID 1182404 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-10 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-55597bd269214294a9ddb85063280212
出典データセット
uspto-grants-2007_10
特許番号
US07288674B2

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