Water → HCID 67350060、化合物

HRID 1676353ノート

反応式

HRID 1676353 の反応式
Cl[C:2](=[O:8])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[CH2:9]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)[CH:10]=[CH2:11].CCN(C(C)C)C(C)C.O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:9]([N:12]([C:13]1[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=1)[C:2](=[O:8])[CH2:3][C:4]([O:6][CH3:7])=[O:5])[CH:10]=[CH2:11]

参加物

7

反応物 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 123460Methyl malonyl chlorideHCID 11829634N-Allyl-N-(4-fluorophenyl)amine

生成物 1

HCID 67350060HCID 67350060、化合物収率 92.2%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Methyl 3-chloro-3-oxopropanoate (9.4 ml, 87 mmol) was added into a solution of N-allyl-4-fluorobenzenamine (12 g, 79 mmol), DIEA (15 ml, 87 mmol) and DMAP (0.97 mg, 7.9 mmol) in CH2Cl2 (200 mL) at 0° C. under nitrogen. The reaction was stirred at 0° C. for 1 hour. The reaction mixture was poured into ice and water, extracted with CH2Cl2, washed with saturated aqueous NaHCO3 and brine. The organic layer was dried with Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography (50% EtOAc in hexane) to afford the product (18.3 g, 92% yield) as brown oil. 1H NMR (400 MHz, CDCl3): δ 7.16-7.22 (m, 2H), 7.08-7.12 (m, 2H), 5.80-5.90 (m, 1H), 5.07-5.17 (m, 2H), 4.27-4.32 (m, 2H), 3.67 (s, 3H), 3.20 (s, 2H).

後処理

  1. extractionextracted with CH2Cl2
  2. washwashed with saturated aqueous NaHCO3 and brine
  3. dry with materialThe organic layer was dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (50% EtOAc in hexane)

出典と根拠

ORDレコード
ord-95b70bbb8539404ea63f0e47de07ef4c
出典データセット
uspto-grants-2011_08
特許番号
US08003662B2

反応ノート

読み込み中…