Methanesulfonic Acid → Ethyl 2-oxo-1-azacyclodecane-10-carboxylate

HRID 21962

반응식

HRID 21962 반응식
[CH2:1]([O:3][C:4]([CH:6]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[O:15])=[O:5])[CH3:2].CS(O)(=O)=O.[N-:21]=[N+]=[N-].[Na+].[OH-].[NH4+]>C(Cl)(Cl)Cl>[O:15]=[C:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[NH:21]1

참가 물질

6

반응물 4

HCID 6395Methanesulfonic AcidHCID 14923Ammonium HydroxideHCID 33557Sodium AzideHCID 107210Ethyl 2-oxocyclononanecarboxylate

생성물 1

HCID 19930826Ethyl 2-oxo-1-azacyclodecane-10-carboxylate

시약·촉매·용매 1

HCID 6212Chloroform용매

반응 조건

온도
0 °C

실험 절차

2-Ethoxycarbonyl-cyclononanone (13.72 g, 64.7 mmol) is dissolved in chloroform (200 mL) and cooled to 0° C. Methanesulfonic acid (62.4 g, 650 mmol) is added, followed by sodium azide (12.68 g, 195 mmol). The reaction is stirred at room temperature for 30 minutes, and then heated to reflux for 4 hours. The reaction mixture is poured onto ice, made basic with concentrated ammonium hydroxide (pH=9), and extracted several times with methylene chloride. The combined organic layers are dried (MgSO4), and the solvent is evaporated. The product is purified by silica gel chromatography (40% ethyl acetate/hexane) to give ethyl 2-oxo-1-azacyclodecane-10-carboxylate, m.p. 101°-103° C.

후처리

  1. temperatureheated
  2. temperatureto reflux for 4 hours
  3. additionThe reaction mixture is poured onto ice
  4. extractionextracted several times with methylene chloride
  5. dry with materialThe combined organic layers are dried (MgSO4)
  6. customthe solvent is evaporated
  7. customThe product is purified by silica gel chromatography (40% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-0576b060cf1e471fa22125ca94b64b1f
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05426103

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