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

HRID 2118346ノート

反応式

HRID 2118346 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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

後処理

  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)

出典と根拠

ORDレコード
ord-8a5d6ff9f23c4a2b82f3ef71fd30b183
出典データセット
uspto-grants-2008_10
特許番号
US07442839B2

反応ノート

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