N-(5-Acetyl-2-benzyloxyphenyl)-N-benzylmethanesulfonamide → N-Benzyl-N-[2-benzyloxy-5-(2-bromoacetyl)phenyl]methanesulfonamide

HRID 2118346노트

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HRID 2118346 반응식
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:8]([N:10]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:11]([CH3:14])(=[O:13])=[O:12])[CH:9]=1)(=[O:3])[CH3:2].[Br-:30].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1>C1COCC1>[Br:30][CH2:2][C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[C:8]([N:10]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:11]([CH3:14])(=[O:13])=[O:12])[CH:9]=1)=[O:3]

참가 물질

4

반응물 2

HCID 12363924N-(5-Acetyl-2-benzyloxyphenyl)-N-benzylmethanesulfonamideHCID 17977687Phenyltrimethylammonium bromide dibromide

생성물 1

HCID 86607679N-Benzyl-N-[2-benzyloxy-5-(2-bromoacetyl)phenyl]methanesulfonamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of N-{5-acetyl-2-[(phenylmethyl)oxy]phenyl}-N-(phenylmethyl) methanesulfonamide (J. Med Chem 1977, 20, 687-92) (1.18 g) in THF (50 ml) was treated with phenyltrimethylammonium tribromide (1.08 g) at <10° and stirred for 6 h. The reaction mixture was quenched with chilled water and then filtered. The filtrate was partitioned between diethyl ether and water, the organic phase was dried (MgSO4) and the solvent was removed in vacuo. The mixture was purified by column chromatography on silica (SPE bond elut, gradient 0 to 45% EtOAc-cyclohexane) to afford the title compound. LCMS RT=3.48 min

후처리

  1. customThe reaction mixture was quenched with chilled water
  2. filtrationfiltered
  3. customThe filtrate was partitioned between diethyl ether and water
  4. dry with materialthe organic phase was dried (MgSO4)
  5. customthe solvent was removed in vacuo
  6. customThe mixture was purified by column chromatography on silica (SPE bond elut, gradient 0 to 45% EtOAc-cyclohexane)

출처 및 근거

ORD 기록
ord-8a5d6ff9f23c4a2b82f3ef71fd30b183
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07442839B2

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