Methanesulfonic Acid → Ethyl 7-oxoazepane-4-carboxylate

HRID 7400

반응식

HRID 7400 반응식
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.[N-:13]=[N+]=[N-].[Na+].CS(O)(=O)=O.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[O:1]=[C:2]1[NH:13][CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1

참가 물질

6

반응물 4

HCID 6395Methanesulfonic AcidHCID 33557Sodium AzideHCID 317638Ethyl 4-oxocyclohexanecarboxylateHCID 516892Sodium Bicarbonate

생성물 1

HCID 23093698Ethyl 7-oxoazepane-4-carboxylate수율 70%

시약·촉매·용매 1

HCID 6212Chloroform용매

반응 조건

온도
10 °C

실험 절차

In a 250 ml three necked flask fitted with reflux condenser, magnetic stirrer and dropping funnel under inert atmosphere, 5.6 ml (5.98 g, 34 mmoles, 1 eq) of ethyl 4-oxocyclohexanecarboxylate 27 were dissolved in 50 ml of CHCl3. 6.65 g (102 mmole, 3 eq) of sodium azide were added, followed by 22.1 ml (32.8 g, 341 mmoles, 10 eq) of methanesulfonic acid dissolved in 20 ml of over 30 min. The mixture was heated to reflux for 1 hour and cooled down to 10° C. 200 nl of saturated sodium bicarbonate solution were added, the mixture decanted and the aqueous phase extracted with 3×150 ml of CHCl3, the combined organic phases were dried over magnesium sulfate, filtered and concentrated to dryness. The residue was purified by PrepLC (800 g SiO2, CH2Cl2/MeOH, 97/3) to give 5.1 g of crude compound. It was crystallised from 40 ml of diethylether to give 4.41 g of pure ester 28, 70% yield.

후처리

  1. temperaturewith reflux condenser, magnetic stirrer
  2. dissolutiondissolved in 20 ml of over 30 min
  3. temperatureThe mixture was heated
  4. temperatureto reflux for 1 hour
  5. customthe mixture decanted
  6. extractionthe aqueous phase extracted with 3×150 ml of CHCl3
  7. dry with materialthe combined organic phases were dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness
  10. customThe residue was purified by PrepLC (800 g SiO2, CH2Cl2/MeOH, 97/3)
  11. customto give 5.1 g of crude compound
  12. customIt was crystallised from 40 ml of diethylether

출처 및 근거

ORD 기록
ord-98c17061ed0941a5ba5bcf3a6530bf66
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087596B2

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