Ammonium Chloride → (R)-4-benzyl-3-((R)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutanoyl)oxazolidin-2-one

HRID 744836노트

반응식

HRID 744836 반응식
C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH2:11]([C@@H:18]1[CH2:22][O:21][C:20](=[O:23])[N:19]1[C:24](=[O:29])[CH2:25][CH:26]([CH3:28])[CH3:27])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH3:30][O:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36]Br)=[CH:34][C:33]=1[O:40][CH2:41][CH2:42][CH2:43][O:44][CH3:45].[Cl-].[NH4+]>O1CCCC1>[CH2:11]([C@@H:18]1[CH2:22][O:21][C:20](=[O:23])[N:19]1[C:24](=[O:29])[C@@H:25]([CH:26]([CH3:27])[CH3:28])[CH2:36][C:35]1[CH:38]=[CH:39][C:32]([O:31][CH3:30])=[C:33]([O:40][CH2:41][CH2:42][CH2:43][O:44][CH3:45])[CH:34]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 11391340(4R)-4-Benzyl-3-(3-methylbutanoyl)-1,3-oxazolidin-2-oneHCID 115583294-(Bromomethyl)-1-methoxy-2-(3-methoxypropoxy)benzene

생성물 1

HCID 22865790(R)-4-benzyl-3-((R)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutanoyl)oxazolidin-2-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
-70 °C

실험 절차

600 ml of tetrahydrofuran are added to a solution of 600 ml of 1M lithium hexamethyl-disilazide and the mixture is stirred at -70° C. Then a solution of 156.6 g of 4(R)-benzyl-3-isovaleroyl-oxazolidin-2-one in 500 ml of tetrahydrofuran is added dropwise and the reaction mixture is stirred for a further 75 minutes at -70° C. Then a solution of 145 g of 4-methoxy-3-(3-methoxypropyloxy)-benzyl bromide in 500 ml of tetrahydrofuran is added dropwise. The temperature of the reaction mixture is allowed to rise from -70° to 0° C. over a period of 2 hours. The reaction mixture is left to stand for a further 18 hours at 4° C. and then, with stirring, 250 ml of saturated ammonium chloride solution are added. The tetrahydrofuran is evaporated off and the residue is extracted with ethyl acetate. The title compound is obtained from the residue of the extracts by purification by means of FC (2.4 kg of silica gel, ethyl acetate/hexane=1:1): Rf (ethyl acetate/hexane=1:2)=0.30; m.p. 55°-56° C.

후처리

  1. stirringthe reaction mixture is stirred for a further 75 minutes at -70° C
  2. waitThe reaction mixture is left
  3. waitto stand for a further 18 hours at 4° C.
  4. stirringwith stirring
  5. customThe tetrahydrofuran is evaporated off
  6. extractionthe residue is extracted with ethyl acetate

출처 및 근거

ORD 기록
ord-75851fa59aa04aa2be1ca20697a5227c
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05559111

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