Felbinac → N-methoxy-N-methyl-4-biphenylacetamide

HRID 449493노트

반응식

HRID 449493 반응식
Cl.[CH3:2][NH:3][O:4][CH3:5].[C:6]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:11]=[CH:10][C:9]([CH2:12][C:13](O)=[O:14])=[CH:8][CH:7]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[C:6]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:11]=[CH:10][C:9]([CH2:12][C:13]([N:3]([O:4][CH3:5])[CH3:2])=[O:14])=[CH:8][CH:7]=1

참가 물질

6

반응물 4

HCID 3332FelbinacHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

생성물 1

HCID 17815837N-methoxy-N-methyl-4-biphenylacetamide수율 70.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

N,O-Dimethylhydroxylamine hydrochloride (550 mg, 5.6 mmol) was added to a mixture of biphenyl-4-ylacetic acid (Aldrich, Cat. #196487) (1 g, 5 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (2.5 g, 5.6 mmol), and N,N-diisopropylethylamine (1.6 mL, 9.4 mmol) in N,N-dimethylformamide (20 mL). The reaction was stirred for 3 h. at r.t., and was partitioned between water and ethyl acetate. The organic phase was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give the crude product, which was purified by Flash chromatography on a silica gel column (EtOAc:Hexane, 1:3 to 1:1) gave 2-biphenyl-4-yl-N-methoxy-N-methylacetamide (0.9 g, 70%) as a white solid. Analytical LCMS (M+H)+: m/z=255.9.

후처리

  1. customwas partitioned between water and ethyl acetate
  2. washThe organic phase was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give the crude product, which
  7. customwas purified by Flash chromatography on a silica gel column (EtOAc:Hexane, 1:3 to 1:1)

출처 및 근거

ORD 기록
ord-c1ffd78b90804dddb0039c68c58076af
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481732B2

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