Toluene → N,N-diisopropyl-6-[(1-trityl-1H-imidazol-4-yl)carbonyl]-2-naphthamide

HRID 724214

反応式

HRID 724214 の反応式
C1(C)C=CC=CC=1.C([Li])CCC.Br[C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[CH:20]=[C:19]([C:24]([N:26]([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])=[O:25])[CH:18]=[CH:17]2.CON(C)C(C[C:39]1[N:40]=[CH:41][N:42]([C:44]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH:43]=1)=O.C1C[O:67][CH2:66]C1>O>[CH:27]([N:26]([CH:30]([CH3:32])[CH3:31])[C:24]([C:19]1[CH:18]=[CH:17][C:16]2[C:21](=[CH:22][CH:23]=[C:14]([C:66]([C:39]3[N:40]=[CH:41][N:42]([C:44]([C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)([C:45]4[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=4)[C:57]4[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=4)[CH:43]=3)=[O:67])[CH:15]=2)[CH:20]=1)=[O:25])([CH3:29])[CH3:28]

参加物

7

反応物 5

HCID 1140TolueneHCID 8028Tetrahydrofuran2 回HCID 218796396-bromo-N,N-diisopropyl-2-naphthamideHCID 54243787N-Methyl-N-methoxy-2-(1-triphenylmethyl-1H-imidazol-4-yl)acetamideHCID 178418339Butyllithium

生成物 1

HCID 21879613N,N-diisopropyl-6-[(1-trityl-1H-imidazol-4-yl)carbonyl]-2-naphthamide

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
-70 °C

実験手順

Dry toluene (20 ml) was cooled to −70° C. and n-butyl lithium (1.6 M; 2.35 ml) was added dropwise. A solution of 6-bromo-N,N-diisopropyl-2-naphthamide (1.20 g) in dry THF (8 ml) was added dropwise to the reaction mixture. After stirring the mixture at −70° C. for 20 min, a solution of N-methoxy-N-methyl-1-trityl-1H-imidazole-4-carboxyamide (1.09 g) in dry THF (6 ml) was added dropwise to the reaction mixture. The mixture was stirred at −70° C. for 20 min and water was added at the same temperature to stop the reaction. The mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography (hexane:ethyl acetate=2:1) to give the title compound (1.40 g) as a colorless powder. The physical and chemical data were identical with those obtained for the compound obtained of Reference Example 13.

後処理

  1. stirringThe mixture was stirred at −70° C. for 20 min
  2. customthe reaction
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by column chromatography (hexane:ethyl acetate=2:1)

出典と根拠

ORDレコード
ord-f83ff25fe42847548c13016112ee2d90
出典データセット
uspto-grants-2006_11
特許番号
US07141598B2

関連ノート

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