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

HRID 21978

반응식

HRID 21978 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 warned 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. customis warned to room temperature
  3. stirringthe reaction is stirred at room temperature for 2.5 hours
  4. customThe reaction is quenched with saturated ammonium chloride
  5. extractionextracted several times with ethyl acetate
  6. dry with materialThe combined organic layers are dried (MgSO4)
  7. customthe solvent is evaporated
  8. customThe product is purified by silica gel chromatography (30% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-abd37e9569de41e18c1a8ba201ccfeea
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05426103

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