Triphenylphosphine → Ethyl {3-[3-(4-hydroxyphenyl)-6-oxo-6H-pyridazin-1-ylmethyl]phenyl}carbamate

HRID 2093348ノート

反応式

HRID 2093348 の反応式
[O:1]=[C:2]1[NH:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11](C(OC(C)(C)C)=O)=[CH:10][CH:9]=2)[CH:4]=[CH:3]1.O[CH2:22][C:23]1[CH:24]=[C:25]([NH:29][C:30](=[O:34])[O:31][CH2:32][CH3:33])[CH:26]=[CH:27][CH:28]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=[O:57]>C1COCC1>[OH:57][C:11]1[CH:10]=[CH:9][C:8]([C:5]2[CH:4]=[CH:3][C:2](=[O:1])[N:7]([CH2:22][C:23]3[CH:24]=[C:25]([NH:29][C:30](=[O:34])[O:31][CH2:32][CH3:33])[CH:26]=[CH:27][CH:28]=3)[N:6]=2)=[CH:13][CH:12]=1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10607893Ethyl (3-hydroxymethylphenyl)carbamateHCID 68516886Tert-butyl 4-(6-oxo-1,6-dihydropyridazin-3-yl)phenyl-carboxylate

生成物 1

HCID 136168092Ethyl {3-[3-(4-hydroxyphenyl)-6-oxo-6H-pyridazin-1-ylmethyl]phenyl}carbamate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

5 g (17.3 mmol) of tert-butyl 4-(6-oxo-1,6-dihydropyridazin-3-yl)phenylcarboxylate, 5.08 g (26 mmol) of ethyl (3-hydroxymethylphenyl)carbamate and 6.8 g (26 mmol) of triphenylphosphine are dissolved in 400 ml of THF. Under a nitrogen atmosphere, the yellow solution is cooled to 0° C., 4.1 ml (26 mmol) of diethyl azodicarboxylate are slowly added dropwise, and the reaction mixture is stirred at room temperature for 20 h. The yellow suspension is evaporated to dryness. The residue is dissolved in 300 ml of dichloromethane, and 40 ml of trifluoroacetic acid are added. The reaction mixture is stirred at room temperature for 20 h, evaporated to dryness, and 100 ml of water, 200 ml of 1N NaOH and 100 ml of ethyl acetate are added to the viscous oil. A precipitate forms in the process, which is filtered off with suction, washed with water and dried in vacuo.

後処理

  1. customThe yellow suspension is evaporated to dryness
  2. dissolutionThe residue is dissolved in 300 ml of dichloromethane
  3. addition40 ml of trifluoroacetic acid are added
  4. stirringThe reaction mixture is stirred at room temperature for 20 h
  5. customevaporated to dryness, and 100 ml of water, 200 ml of 1N NaOH and 100 ml of ethyl acetate
  6. additionare added to the viscous oil
  7. filtrationA precipitate forms in the process, which is filtered off with suction
  8. washwashed with water
  9. customdried in vacuo

出典と根拠

ORDレコード
ord-71a13cad771748e5879a041cf80ad760
出典データセット
uspto-grants-2013_05
特許番号
US08445489B2

反応ノート

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