Citric Acid → N-hydroxy-2-phenylacetamide

HRID 9930

반응식

HRID 9930 반응식
[C:1]1([CH2:7][C:8]([O:10]C)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:12][OH:13].[C-]#N.[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CO>[OH:13][NH:12][C:8](=[O:10])[CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

7

반응물 4

HCID 311Citric AcidHCID 787HydroxylamineHCID 7559Methyl phenylacetateHCID 9032Potassium Cyanide

생성물 1

HCID 220184N-hydroxy-2-phenylacetamide수율 77%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To methyl phenylacetate (0.288 mL, 2.0 mmol) in THF:MeOH: 50% aqueous NH2OH (1:1:0.5, 2.5 mL) was added KCN (5 mg, 0.08 mmol, 4 mol %) and the mixture was stirred at ambient temperature. After 2 h the reaction was complete by HPLC. To the mixture was added saturated aqueous citric acid (25 mL) followed by extraction with EtOAc (3×25 mL). The organic phase was isolated, dried (MgSO4), filtered, and the filtrate was concentrated in vacuo to give a residue. The residue was purified by reverse phase HPLC (C-18, 5μ 100×30 mm column), eluting with a gradient of acetonitrile: water (0.05% TFA). Following lyophilization of the product fractions there was obtained pure N-hydroxy-2-phenylacetamide as a fluffy solid (0.234 g, 77% yield): LRMS (M+H)+: 152.1 m/z; 1H NMR (DMSO-d6) δ: 10.6(s, 1H), 8.81(s, 1H), 7.2(m, 5H), 3.26(s, 2H); Anal (C,H,N): % C: (calc) 63.56; (found) 63.63; % H: (calc.) 6.00; (found) 5.91; % N: (calc.) 9.27, (found) 9.04.

후처리

  1. extractionfollowed by extraction with EtOAc (3×25 mL)
  2. customThe organic phase was isolated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customto give a residue
  7. customThe residue was purified by reverse phase HPLC (C-18, 5μ 100×30 mm column)
  8. washeluting with a gradient of acetonitrile

출처 및 근거

ORD 기록
ord-645a5165719843d689ffc71ed8b89810
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091378B2

연결된 노트

불러오는 중…