Phenylacetic Acid → N-hydroxy-2-phenylacetamide

HRID 1937034

반응식

HRID 1937034 반응식
C=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl.CN(C)CCCN=C=NCC.C1(CC(O)=[O:29])C=CC=CC=1.C[N:32]([CH:34]=[O:35])C>>[OH:29][NH:32][C:34](=[O:35])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

참가 물질

5

반응물 4

HCID 999Phenylacetic AcidHCID 6228DimethylformamideHCID 7501StyreneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

생성물 1

HCID 220184N-hydroxy-2-phenylacetamide수율 39%

실험 절차

To a suspension of the 4-(methyl-O-methylhydroxylamine)-2-fluorophenoxymethyl-copoly(styrene-1% divinylbenzene)resin (0.10 g, 0.14 mmol) in dry DMF (2 ml) is added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.08 g, 0.42 mmol, 3 eq.). To the mixture is then added phenylacetic acid (0.06 g, 0.42 mmol, 3 eq.). The mixture is shaken overnight. The resin is filtered and washed with DMF (×5), THF: H2O (3:1, ×5), THF (×3), MeOH (×3) and DCM (×3). To the resin is added TFA (1 ml) and DCM (1 ml) and the mixture shaken for 1 hour. The mixture is filtered into a tared vial and the resin washed with DCM (×2) and toluene (×2). The combined filtrates are evaporated in vacuo to yield N-hydroxy-phenyl-acetamide (0.0084 g, 39%). LCMS gives 151 [M+].

후처리

  1. filtrationThe resin is filtered
  2. washwashed with DMF (×5), THF: H2O (3:1, ×5), THF (×3), MeOH (×3) and DCM (×3)
  3. additionTo the resin is added TFA (1 ml) and DCM (1 ml)
  4. stirringthe mixture shaken for 1 hour
  5. filtrationThe mixture is filtered into a tared vial and the resin
  6. washwashed with DCM (×2) and toluene (×2)
  7. customThe combined filtrates are evaporated in vacuo

출처 및 근거

ORD 기록
ord-5bf10fc4d4e54836a3efba8ef0e475dd
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06392010B1

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