Hydrochloric Acid → HCID 178472438、化合物

HRID 1631435ノート

反応式

HRID 1631435 の反応式
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.Cl.C([O-])([O-])=O.[K+].[K+].Br[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(#N)C>[CH2:21]([N:1]([CH2:8][C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1)[C@H:2]1[CH2:3][CH2:4][C@H:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:7]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178472434HCID 178472434、化合物

生成物 1

HCID 178472438HCID 178472438、化合物収率 91%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

A stirred suspension of 13A.HCl (5.12 g, 24.65 mmol) in acetonitrile (75 mL) was treated with K2CO3 (13.63 g, 99 mmol) and (bromomethyl)benzene (7.32 mL, 61.6 mmol). The resulting suspension was stirred at 80° C. overnight. Upon cooling, the solid was filtered off and filtrate was concentrated. The residue was purified by Isco silica column (80 g) eluted with ethyl acetate-hexane: 0%-20%. Concentration of the appropriate fractions provided 13B (7.92 g, 91% yield) as a colorless oil. MS (ES): m/z=352.2 [M+H]+. 1H NMR (400 MHz, CDCl3) δ ppm 7.08-7.34 (m, 10H); 4.01 (q, 2H, J=7.1 Hz); 3.55 (s, 4H); 2.40-2.49 (m, 1H); 2.06-2.14 (m, 1H); 1.86-2.00 (m, 2H); 1.24-1.38 (m, 2H); 1.18 (t, 3H, J=7.1 Hz).

後処理

  1. temperatureUpon cooling
  2. filtrationthe solid was filtered off
  3. concentrationfiltrate was concentrated
  4. customThe residue was purified by Isco silica column (80 g)
  5. washeluted with ethyl acetate-hexane

出典と根拠

ORDレコード
ord-28fba15365064698af6abff01dc18eab
出典データセット
uspto-grants-2014_07
特許番号
US08791257B2

反応ノート

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