Ethyl Acetate → (E)-(R)-2-((S)-1-Hydroxy-2-morpholin-4-yl-2-oxo-ethyl)-5-phenyl-pent-4-enoic acid methyl ester

HRID 1830156노트

반응식

HRID 1830156 반응식
C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH3:11][O:12][C:13](=[O:25])[CH2:14][C@H:15]([OH:24])[C:16]([N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)=[O:17].[CH2:26](Br)[CH:27]=[CH:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(OCC)(=O)C>C1COCC1.C(Cl)Cl>[CH3:11][O:12][C:13](=[O:25])[C@@H:14]([C@H:15]([OH:24])[C:16]([N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)=[O:17])[CH2:26]/[CH:27]=[CH:28]/[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 98116BromomethylstyreneHCID 2733832Lithium HexamethyldisilazideHCID 58619497(S)-3-Hydroxy-4-morpholin-4-yl-4-oxo-butyric acid methyl ester

생성물 1

HCID 69437384(E)-(R)-2-((S)-1-Hydroxy-2-morpholin-4-yl-2-oxo-ethyl)-5-phenyl-pent-4-enoic acid methyl ester

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

Lithium hexamethyldisilazide (1M in THF, 14.5 ml, 14.5 mmol) was added to a solution of (S)-3-Hydroxy-4-morpholin-4-yl-4-oxo-butyric acid methyl ester (1.5 g, 6.9 mmol) in dry THF (15 ml) at −78° C. under N2 and stirred for 30 min. Cinnamyl bromide (1.6 g, 7.32 mmol) was then added, the reaction mixture stirred at −78° C. for 2 hrs, warmed up to room temperature and stirred overnight at room temperature. The reaction was quenched with saturated ammonium chloride solution, adjusted the pH to 6 with 1N HCl and extracted with ethyl acetate. Combined ethyl acetate extracts were dried over MgSO4 and concentrated under reduced pressure to give pale brown solid. Column chromatography on silica eluting with a mixture of ethyl acetate and methylene chloride gave the title compound as pale, yellow solid (1.15 g).

후처리

  1. stirringthe reaction mixture stirred at −78° C. for 2 hrs
  2. stirringstirred overnight at room temperature
  3. customThe reaction was quenched with saturated ammonium chloride solution
  4. extractionextracted with ethyl acetate
  5. dry with materialCombined ethyl acetate extracts were dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customto give pale brown solid

출처 및 근거

ORD 기록
ord-307ab29c2ecd4ce99ea21443a4be1894
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07064123B1

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