Potassium Iodide → Ethyl 7-Bromo-3-(3-(tert.-butoxycarbonylamino)propoxy)-naphthalen-2-carboxylate

HRID 2187640노트

반응식

HRID 2187640 반응식
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([OH:17])[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9]2)=[CH:4][CH:3]=1.[C:18]([O:22][C:23]([NH:25][CH2:26][CH2:27][CH2:28]Cl)=[O:24])([CH3:21])([CH3:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C.O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([O:17][CH2:28][CH2:27][CH2:26][NH:25][C:23]([O:22][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:24])[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9]2)=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 10932310N-Boc-3-ChloropropylamineHCID 18476207Ethyl 7-bromo-3-hydroxy-2-naphthoate

생성물 1

HCID 18476258Ethyl 7-Bromo-3-(3-(tert.-butoxycarbonylamino)propoxy)-naphthalen-2-carboxylate수율 100%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of 3.8 g (12.88 mmol) ethyl 7-bromo-3-hydroxynaphthalen-2-carboxylate, 3.0 g (15.5 mmol) 1-(tert.-butoxycarbonylamino)-3-chloropropane (prepared according to Helv. Chim. Acta 76 (1993), 1644), 2.0 g (14.5 mmol) potassium carbonate, and a catalytic amount of potassium iodide in 20 ml dry DMF was stirred at 90° C. for 6 h. It was poured into water, extracted three times with ethyl acetate, and the combined organic layers were washed three times with water, dried over sodium sulfate, and concentrated in vacuo. The intermediate was purified by chromatography on silica gel with toluene/acetone 9:1 to give 5.8 g (100%) of a yellow oil, which solidified rapidly upon standing.

후처리

  1. extractionextracted three times with ethyl acetate
  2. washthe combined organic layers were washed three times with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe intermediate was purified by chromatography on silica gel with toluene/acetone 9:1

출처 및 근거

ORD 기록
ord-6b5b9054a9464b6a999f6674ec845ef5
출처 데이터셋
uspto-grants-2002_06
특허 번호
US06410562B1

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