4-(Bromomethyl)benzoic acid → N-{1-[(Cyano-dimethyl-methyl)-carbamoyl]-3-methyl-butyl)-4-bromomethyl-benzamide

HRID 276708ノート

反応式

HRID 276708 の反応式
[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.C1C=CC2N(O)N=NC=2C=1.[C:22]([C:24]([NH:27][C:28](=[O:35])[CH:29]([NH2:34])[CH2:30][CH:31]([CH3:33])[CH3:32])([CH3:26])[CH3:25])#[N:23]>CN(C)C=O>[C:22]([C:24]([NH:27][C:28]([CH:29]([NH:34][C:7](=[O:9])[C:6]1[CH:5]=[CH:4][C:3]([CH2:2][Br:1])=[CH:11][CH:10]=1)[CH2:30][CH:31]([CH3:32])[CH3:33])=[O:35])([CH3:26])[CH3:25])#[N:23]

参加物

5

反応物 3

HCID 225994-(Bromomethyl)benzoic acidHCID 757711-HydroxybenzotriazoleHCID 539013662-Amino-4-methyl-pentanoic acid (cyano-dimethyl-methyl)-amide

生成物 1

HCID 18316679N-{1-[(Cyano-dimethyl-methyl)-carbamoyl]-3-methyl-butyl)-4-bromomethyl-benzamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

4-Bromomethylbenzoic acid (4.1 mmol), HOBt (4.1 mmol) and WSCD.HCI (4.1 mmol) are dissolved in dimethylformamide (7 ml) and stirred for 10 min. 2-Amino-4-methyl-pentanoic acid (cyano-dimethyl-methyl)-amide (4.1 mmol) is added in DMF (3 ml) and the reaction mixture is stirred at RT overnight. After evaporation of the solvent, the residue is extracted with ethyl acetate. The extract is washed with water, 10% citric acid, brine, sodium bicarbonate, brine and dried over magnesium sulfate and evaporated. The crude product is suspended in diethylether and the solid filtered of and dried (vacuum). A white powder with mp. 185-187° C., Rf=0.43 (n-hexane:ethyl acetate=1:1) is obtained.

後処理

  1. stirringthe reaction mixture is stirred at RT overnight
  2. customAfter evaporation of the solvent
  3. extractionthe residue is extracted with ethyl acetate
  4. washThe extract is washed with water, 10% citric acid, brine, sodium bicarbonate, brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. filtrationthe solid filtered of and
  8. customdried (vacuum)
  9. customA white powder with mp. 185-187° C., Rf=0.43 (n-hexane:ethyl acetate=1:1) is obtained

出典と根拠

ORDレコード
ord-3519902a1dbb48f2b0966711c6a79c4f
出典データセット
uspto-grants-2002_03
特許番号
US06353017B1

反応ノート

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