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

HRID 889271노트

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HRID 889271 반응식
[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

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 15219197HCID 15219197, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-84bc523a57de4e5baf62d1c7e360d8fe
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08252820B2

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