tert-Butyl Dimethylphosphonoacetate → Ethyl 3-t-butoxycarbonylmethylidene-2-oxo-1-azacyclodecane-10-carboxylate

HRID 5405

반응식

HRID 5405 반응식
COP([CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])(OC)=O.[O:15]=[C:16]1[C:25](=O)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH:18]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[NH:17]1>C1(C)C=CC=CC=1.C1COCC1>[C:11]([O:10][C:8]([CH:7]=[C:25]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH:18]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[NH:17][C:16]1=[O:15])=[O:9])([CH3:12])([CH3:13])[CH3:14]

참가 물질

5

반응물 2

HCID 4564495tert-Butyl DimethylphosphonoacetateHCID 19930804Ethyl 2,3-di-oxo-1-azacyclodecane-10-carboxylate

생성물 1

HCID 54383214Ethyl 3-t-butoxycarbonylmethylidene-2-oxo-1-azacyclodecane-10-carboxylate

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매2회

실험 절차

Potassium hexamethyldisilylamide (40.5 mL of a 0.58M solution in toluene, 23.5 mmol) is added to THF (60 mL), and then cooled to 0° C. t-Butyl dimethylphosphonoacetate (4.6 mL, 23.5 mmol) is added dropwise, and the reaction is warmed to room temperature and stirred for 25 minutes. Ethyl 2,3-di-oxo-1-azacyclodecane-10-carboxylate (2.83 g, 11.74 mmol) is added in THF (15 mL), and the reaction is stirred at room temperature for 2.5 hours. The reaction is quenched with saturated ammonium chloride, and then extracted several times with ethyl acetate. The combined organic layers are dried (MgSO4), and the solvent is evaporated. The product is purified by silica gel chromatography (30% ethyl acetate/hexane) to give ethyl 3-t-butoxycarbonylmethylidene-2-oxo-1-azacyclodecane-10-carboxylate.

후처리

  1. additionis added dropwise
  2. stirringthe reaction is stirred at room temperature for 2.5 hours
  3. customThe reaction is quenched with saturated ammonium chloride
  4. extractionextracted several times with ethyl acetate
  5. dry with materialThe combined organic layers are dried (MgSO4)
  6. customthe solvent is evaporated
  7. customThe product is purified by silica gel chromatography (30% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-9f6126e0435c45d1b9864f1d5abc955e
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05244889

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