Benzyl Bromide → 3-[Benzyl-(pyridine-3-sulfonyl)-amino]-benzoic acid

HRID 62817

反応式

HRID 62817 の反応式
C([O:5][C:6](=[O:23])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][S:14]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)(=[O:16])=[O:15])[CH:8]=1)(C)(C)C.[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C.FC(F)(F)C(O)=O.ClCCl>[CH2:24]([N:13]([S:14]([C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)(=[O:15])=[O:16])[C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=1)[C:6]([OH:5])=[O:23])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

参加物

7

反応物 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 673108723-(Pyridine-3-sulfonylamino)-benzoic acid tert-butyl ester

生成物 1

HCID 673107893-[Benzyl-(pyridine-3-sulfonyl)-amino]-benzoic acid収率 53.1%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒HCID 21863450Trifluoroacetic acid methylene chloride溶媒

実験手順

A solution of 3-(Pyridine-3-sulfonylamino)-benzoic acid tert-butyl ester (99 mg, 0.3 mmol), benzyl bromide (39 μL, 0.32 mmol) and Cesium Carbonate (145 mg, 0.4 mmol) in dimethylformamide (5 ml) was stirred for 16 hrs. The reaction was diluted with ethyl acetate (50 ml) and washed with water (6×100 ml). The organic layer was separated, dried over magnesium sulfate and concentrated in vacuo to give a yellow oil. The oil was dissolved in trifluoroacetic acid/dichloromethane (1:5 v/v) (10 ml), stirred for 3 hrs and then concentrated in vacuo to afford the title compound as a white solid (58.7 mg). HPLC retention time 4.31 min. Mass spectrum (APCI+) m/z 369 (M+H).

後処理

  1. washwashed with water (6×100 ml)
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a yellow oil
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-95c46d306a314f198fa1f310bd5902d8
出典データセット
uspto-grants-2016_09
特許番号
US09447033B2

関連ノート

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