2,4-Dichlorophenol → HCID 56649063、化合物

HRID 537082ノート

反応式

HRID 537082 の反応式
[P:1](Cl)(Cl)(=[O:9])[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[OH:20].C(N(CC)CC)C.[CH:28]([O:31][C:32](=[O:36])[C@H:33]([CH3:35])[NH2:34])([CH3:30])[CH3:29]>C(Cl)Cl.C(OCC)(=O)C.CCCCCC>[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[O:20][P:1]([NH:34][C@@H:33]([CH3:35])[C:32]([O:31][CH:28]([CH3:30])[CH3:29])=[O:36])([O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:9]

参加物

7

反応物 4

HCID 84492,4-DichlorophenolHCID 8471Triethylamine2 回HCID 13038Phosphorodichloridic acid, phenyl esterHCID 13089460L-Alanine Isopropyl Ester

生成物 1

HCID 56649063HCID 56649063、化合物収率 66%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 21226206Ethyl acetate hexane溶媒

反応条件

温度
-78 °C

実験手順

Phenyl phosphorodichloridate (10.0 g, 47.4 mmol) was dissolved in 60 mL of dry DCM and subsequently cooled to −78° C. Slow addition of a preformed mixture of 2,4-dichlorophenol (7.73 g, 47.4 mmol) and triethylamine (7.27 mL, 52.1 mmol) in 20 mL of DCM was followed by stirring at above temperature for 30 min. The reaction was brought to 0° C. and stirred for 2.5 h at this temperature before (L)-alanine isopropyl ester (7.95 g, 47.4 mmol) was added as a solid in one batch. Stirring for 40 min at 0° C. was then followed by addition of more triethylamine (13.9 mL, 99.54 mmol) and additional stirring for 3 h at 0° C. or until judged complete by TLC (ethyl acetate/hexane=1/3). The reaction mixture was subsequently evaporated under reduced pressure and finally submitted to column chromatography (ethyl acetate in hexane) on silica gel to yield the product 122 (mixture of two isomers) in 66% yield (13.6 g) as viscous colorless oil.

後処理

  1. customwas brought to 0° C.
  2. additionwas added as a solid in one batch
  3. stirringStirring for 40 min at 0° C.
  4. stirringadditional stirring for 3 h at 0° C.
  5. customThe reaction mixture was subsequently evaporated under reduced pressure

出典と根拠

ORDレコード
ord-b6c7a5602e0c438ea14f7ae8d3ba9c43
出典データセット
uspto-grants-2014_10
特許番号
US08859756B2

反応ノート

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