Ethyl Acetate → Methyl 2-(2-benzyloxy-6-fluoroanilino)-acetate

HRID 889271ノート

反応式

HRID 889271 の反応式
[CH2:1]([O:8][C:9]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:10]=1[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:18][C:19]([O:21][CH3:22])=[O:20].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:10]=1[NH:11][CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 15219197HCID 15219197、化合物

生成物 1

HCID 68430918Methyl 2-(2-benzyloxy-6-fluoroanilino)-acetate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

A mixture of 2-benzyloxy-6-fluoroaniline (950 mg, 4.37 mmol), methyl bromoacetate (456 μL, 737 mg, 4.82 mmol), and potassium carbonate (1.21 g, 8.76 mmols) in DMF (10 mL) is heated at 60° C. for 18 h. The mixture is poured into ethyl acetate and extracted once with water and five times with brine. The organic layer is dried, filtered, and the solvent removed under reduced pressure to afford a crude oil that is chromatographed on an Isco Companion (80 g silica gel, 0-30% gradient of hexane/ethyl acetate) to afford methyl 2-(2-benzyloxy-6-fluoroanilino)-acetate as an oil. MS (M+1)+=290; NMR (CDCl3): δ 7.39 (m, 5H), 6.67 (m, 3H), 5.10 (s, 2H), 4.57 (br s, 1H), 4.11 (m, 2H), 3.72 (s, 3H).

後処理

  1. extractionextracted once with water and five times with brine
  2. customThe organic layer is dried
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure
  5. customto afford a crude oil that
  6. customis chromatographed on an Isco Companion (80 g silica gel, 0-30% gradient of hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-84bc523a57de4e5baf62d1c7e360d8fe
出典データセット
uspto-grants-2012_08
特許番号
US08252820B2

反応ノート

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