Diethyl cyclopropane-1,1-dicarboxylate → HCID 68956592, 화합물

HRID 2378072노트

반응식

HRID 2378072 반응식
C([Li])CCC.[C:6]([Si:10]([CH3:29])([CH3:28])[O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[N:26][OH:27])[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:14][CH:13]=1)([CH3:9])([CH3:8])[CH3:7].[C:30]1([C:38](OCC)=[O:39])([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:32][CH2:31]1>C1COCC1>[CH2:36]([O:35][C:33]([C:30]1([C:38]2([OH:39])[O:27][N:26]=[C:18]([C:15]3[CH:16]=[CH:17][C:12]([O:11][Si:10]([C:6]([CH3:7])([CH3:9])[CH3:8])([CH3:29])[CH3:28])=[CH:13][CH:14]=3)[CH:19]2[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:32][CH2:31]1)=[O:34])[CH3:37]

참가 물질

5

반응물 3

HCID 73790Diethyl cyclopropane-1,1-dicarboxylateHCID 72579577HCID 72579577, 화합물HCID 178418339Butyllithium

생성물 1

HCID 68956592HCID 68956592, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

n-Butyllithium (2.5 M in hexane, 983.8 mL) is added to a solution of 1-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2-phenyl-ethanone oxime, which may be produced as in Example 136 (400 g) in THF (4 L) at 0° C. and the reaction solution is stirred for one hour at this temperature. Diethyl 1,1-cyclopropanedicarboxylate (227 mL) is added to the reaction solution, stirred for one hour at 0° C. and then the reaction is quenched with saturated ammonium chloride, diluted with ethyl acetate, washed with water, brine, dried over anhydrous sodium sulfate, filtered, and the filtrate evaporated under reduced pressure. The crude product is purified by column chromatography with 5-10% ethyl acetate in hexane to give a light yellow solid, which is triturated with pentane and filtered to give 1-{3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-5-hydroxy-4-phenyl-4,5-dihydro-isoxazol-5-yl}-cyclopropanecarboxylic acid ethyl ester (230.8 g.)

후처리

  1. stirringstirred for one hour at 0° C.
  2. customthe reaction is quenched with saturated ammonium chloride
  3. additiondiluted with ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe filtrate evaporated under reduced pressure
  8. customThe crude product is purified by column chromatography with 5-10% ethyl acetate in hexane
  9. customto give a light yellow solid, which
  10. customis triturated with pentane
  11. filtrationfiltered

출처 및 근거

ORD 기록
ord-d550e11fe0204cedb1cd8de31ba8aa84
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07470715B2

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