Toluene → HCID 23134773、化合物

HRID 2220151ノート

反応式

HRID 2220151 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].Br[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:26])[C:22]([O:24][CH3:25])=[O:23])=[CH:17][CH:16]=1.C(N(C(C)C)CC)(C)C.C1(C)C=CC=CC=1>O1CCOCC1>[CH2:8]([O:7][C:5]([C:4]1[CH:3]=[C:2]([NH:1][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21](=[O:26])[C:22]([O:24][CH3:25])=[O:23])=[CH:19][CH:20]=2)[CH:12]=[CH:11][CH:10]=1)=[O:6])[CH3:9]

参加物

6

反応物 4

HCID 1140TolueneHCID 11400Ethyl 3-aminobenzoateHCID 81531DiisopropylethylamineHCID 14916089Methyl 4-(bromomethyl)-α-oxobenzeneacetate

生成物 1

HCID 23134773HCID 23134773、化合物

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
60 °C

実験手順

To a solution of ethyl 3-aminobenzoate (7.3 ml) and methyl 2-[4-(bromomethyl)phenyl]-2-oxoacetate (6.4 g) in dioxane (40 ml) was added diisopropylethylamine (6.4 ml), and the mixture was stirred at 60° C. for 2 hrs. The mixture was allowed to return to room temperature and toluene (330 ml) was added. The mixture was left standing at 0° C. for 5 hrs and the precipitated diisopropylethylamine hydrobromide was filtered off. The filtrate was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate and water. The ethyl acetate layer was separated, washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane-ethyl acetate:4-1 v/v) to give the object compound (7.61 g) as a syrup.

後処理

  1. customto return to room temperature
  2. waitThe mixture was left
  3. waitstanding at 0° C. for 5 hrs
  4. filtrationthe precipitated diisopropylethylamine hydrobromide was filtered off
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. dissolutionthe residue was dissolved in ethyl acetate
  7. customThe ethyl acetate layer was separated
  8. washwashed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-3c4107cb7271420eafae2ff9ee63e833
出典データセット
uspto-grants-2008_08
特許番号
US07417052B2

反応ノート

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