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

HRID 1796151ノート

反応式

HRID 1796151 の反応式
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

参加物

7

反応物 4

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

生成物 1

HCID 69437384(E)-(R)-2-((S)-1-Hydroxy-2-morpholin-4-yl-2-oxo-ethyl)-5-phenyl-pent-4-enoic acid methyl ester収率 50%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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 yellow 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).

後処理

  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 yellow solid

出典と根拠

ORDレコード
ord-c760e8a45e844358bcd08023211adf67
出典データセット
uspto-grants-2006_04
特許番号
US07030116B2

反応ノート

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