Citric Acid → 2-Ethoxycarbonyl-3-[1-(4-fluoro-phenyl)-meth-(E)-ylidene]-4-methyl-pentanedioic acid 1-tert-butyl ester 5-ethyl ester

HRID 1644710

反応式

HRID 1644710 の反応式
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH3:2].CC(C)([O-])C.[K+].[CH2:20]([O:22][C:23](=[O:35])[C:24]([CH3:34])=[C:25]=[CH:26][C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1)[CH3:21].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C(=O)C>[CH2:20]([O:22][C:23](=[O:35])[CH:24]([CH3:34])/[C:25](=[CH:26]\[C:27]1[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=1)/[CH:5]([C:4]([O:3][CH2:1][CH3:2])=[O:13])[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH3:21]

参加物

6

反応物 4

HCID 311Citric AcidHCID 96345tert-Butyl ethyl malonateHCID 11481404HCID 11481404、化合物HCID 23665647Potassium tert-butoxide

生成物 1

HCID 593265542-Ethoxycarbonyl-3-[1-(4-fluoro-phenyl)-meth-(E)-ylidene]-4-methyl-pentanedioic acid 1-tert-butyl ester 5-ethyl ester

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
25 °C

実験手順

Malonic acid tert-butyl ester ethyl ester (30.08 g, 151.8 mmol) was added to a solution of potassium tert-butoxide (16.30 g, 138.0 mmol) in 200 mL of N,N-dimethyl acetamide, while the reaction temperature was maintained at ˜25° C. To the resulting mixture was then added the solution of 4-(4-fluoro-phenyl)-2-methyl-buta-2,3-dienoic acid ethyl ester prepared above, at such a rate that the reaction temperature was maintained between 20-28° C. After the addition was complete, the reaction mixture was stirred at room temperature for 20 minutes, when HPLC indicated completed reaction. The mixture was then treated with 100 mL of 1M citric acid and 150 mL of ice-water, and then extracted with 400 mL of methyl tert-butyl ether. The organic extract was separated and washed with 2×200 mL of water, and then concentrated to produce 56.36 g of a yellow oil, which was used in the next step without further purification.

後処理

  1. customprepared above, at such a rate that the reaction temperature
  2. temperaturewas maintained between 20-28° C
  3. additionAfter the addition
  4. customreaction
  5. extractionextracted with 400 mL of methyl tert-butyl ether
  6. extractionThe organic extract
  7. customwas separated
  8. washwashed with 2×200 mL of water
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-2756807afef94cedbe33fd59b19713b7
出典データセット
uspto-grants-2012_02
特許番号
US08124629B2

関連ノート

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