반응식
[CH2:1]([O:3][C:4](=[O:14])[CH2:5]P(OCC)(OCC)=O)[CH3:2].C([Li])CCC.[C:20]([O:24][C:25](=[O:47])[NH:26][C@:27]([CH:45]=O)([CH3:44])[CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])=[CH:32][CH:31]=1)([CH3:23])([CH3:22])[CH3:21].C([O-])(O)=O.[Na+]>C1COCC1.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:14])/[CH:5]=[CH:45]/[C@@:27]([NH:26][C:25]([O:24][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:47])([CH3:44])[CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])=[CH:32][CH:31]=1)[CH3:2]참가 물질
반응물 4
생성물 1
시약·촉매·용매 2
반응 조건
- 온도
- -78 °C
실험 절차
To a stirred solution of (diethoxy-phosphoryl)-acetic acid ethyl ester (429 mg, 1.92 mMol) in dry THF (7 ml) is added n-butyllithium (0.66 ml, 2.5M in hexane, 1.66 mMol) at −78° C. The mixture was stirred at −78° C. for 1 hour. After that time, a solution of [(R)-1-formyl-3-(4-heptyloxy-phenyl)-1-methyl-propyl]-carbamic acid tert-butyl ester (500 mg, 1.28 mMol) in THF (4 ml) is added and stirring is continued at −78° C. for 1.5 hours. The mixture is allowed to warm to RT and then stirred at RT for 2 hours. The reaction mixture is then poured onto a biphasic mixture of AcOEt and NaHCO3 (saturated aqueous solution) and the aqueous phase is extracted twice with AcOEt. The combined organic layers are dried (Na2SO4) and concentrated under reduced pressure. Column chromatography eluting with 4% AcOEt in toluene gives the title compound as a colourless oil.
후처리
- stirringstirring
- waitis continued at −78° C. for 1.5 hours
- temperatureto warm to RT
- stirringstirred at RT for 2 hours
- extractionthe aqueous phase is extracted twice with AcOEt
- dry with materialThe combined organic layers are dried (Na2SO4)
- concentrationconcentrated under reduced pressure
- washColumn chromatography eluting with 4% AcOEt in toluene
출처 및 근거
- ORD 기록
- ord-e219271ff5654914b84b2a1a70a9aa35
- 출처 데이터셋
- uspto-grants-2010_06
- 특허 번호
- US07728020B2
연결된 노트
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