Ethyl bromoacetate → HCID 66879905、化合物

HRID 1893539ノート

反応式

HRID 1893539 の反応式
[C:1]([O:5][C:6](=[O:15])[C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]([CH3:14])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].C(N([CH2:30][CH3:31])C(C)C)(C)C>C(OCC)(=O)C>[CH2:21]([O:20][C:18](=[O:19])[CH2:17][N:13]([CH2:7][C:6]([O:15][CH2:30][CH3:31])=[O:5])[C:10]1[CH:11]=[CH:12][C:7]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:15])=[CH:8][C:9]=1[CH3:14])[CH3:22]

参加物

5

反応物 3

HCID 7748Ethyl bromoacetateHCID 81531DiisopropylethylamineHCID 53432587tert-Butyl 4-amino-3-methylbenzoate

生成物 1

HCID 66879905HCID 66879905、化合物

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
140 °C

実験手順

The compound (51.5 g) obtained in step B, ethyl bromoacetate (160 ml, 1.44 mol) and N,N-diisopropylethylamine (250 ml, 1.47 mol) were mixed, and the mixture was stirred with heating at 140° C. for 10 hr. The reaction mixture was cooled, diluted with ethyl acetate, and the organic layer was washed with 20% aqueous citric acid solution and saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane) to give a mixture of the title compound and N-(4-tert-butoxycarbonyl-2-methyl)phenylglycine ethyl ester. To this mixture were added ethyl bromoacetate (80 ml, 719 mmol) and N,N-diisopropylethylamine (125 ml, 735 mmol), and the mixture was stirred again with heating at 140° C. for 11 hr, which was followed by the purification similar to the above to give the title compound (95.3 g) as a yellow oil.

後処理

  1. temperatureThe reaction mixture was cooled
  2. washthe organic layer was washed with 20% aqueous citric acid solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe insoluble material was filtered off
  5. concentrationthe solution was concentrated under reduced pressure
  6. customThe obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane)
  7. customto give

出典と根拠

ORDレコード
ord-ec156923af8d43ba991138ed71fcf1e0
出典データセット
uspto-grants-2013_08
特許番号
US08513235B2

反応ノート

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