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

HRID 1518991

반응식

HRID 1518991 반응식
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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매HCID 21863450Trifluoroacetic acid methylene chloride용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1e2854c607dc49b2a3de6fbc6f9ea338
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073834B2

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