Morpholine → (S)-N-[[3-[3-fluoro-4-[4-[3-(4-morpholinyl)-1-oxopropyl]-1-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

HRID 1940659

반응식

HRID 1940659 반응식
[N:1]1([CH2:7][CH2:8][C:9]([OH:11])=O)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.N1CCOCC1.C(OCC)(=O)C=C.C1(N=C=NC2CCCCC2)CCCCC1.[F:40][C:41]1[CH:42]=[C:43]([N:53]2[CH2:57][C@H:56]([CH2:58][NH:59][C:60](=[O:62])[CH3:61])[O:55][C:54]2=[O:63])[CH:44]=[CH:45][C:46]=1[N:47]1[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1>CN(C)C1C=CN=CC=1.O1CCCC1.ClCCl.C(O)C>[F:40][C:41]1[CH:42]=[C:43]([N:53]2[CH2:57][C@H:56]([CH2:58][NH:59][C:60](=[O:62])[CH3:61])[O:55][C:54]2=[O:63])[CH:44]=[CH:45][C:46]=1[N:47]1[CH2:52][CH2:51][N:50]([C:9](=[O:11])[CH2:8][CH2:7][N:1]2[CH2:2][CH2:3][O:4][CH2:5][CH2:6]2)[CH2:49][CH2:48]1

참가 물질

9

반응물 5

HCID 8083MorpholineHCID 8821Ethyl AcrylateHCID 10868DicyclohexylcarbodiimideHCID 4108133-(Morpholin-4-yl)propanoic acidHCID 10520848(S)-N-((3-(3-fluoro-4-(piperazin-1-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide

생성물 1

HCID 53713601(S)-N-[[3-[3-fluoro-4-[4-[3-(4-morpholinyl)-1-oxopropyl]-1-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide수율 95%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 702Ethanol용매HCID 21919333Tetrahydrofurane dichloromethane용매

실험 절차

3-(4-Morpholinyl)propionic acid (0.600 g, 2.11 mmol), prepared by condensation of morpholine with ethyl acrylate (3 equivalents) in refluxing ethanol, followed by distillation, saponification (1N aqueous sodium hydroxide, tetrahydrofuran, reflux), neutralization (1N HCl) and lyophilization, was combined with 1,3-dicyclohexylcarbodiimide (0.434 g, 2.11 mmol), 4-(dimethylamino)pyridine (13 mg, 0.11 mmol), (S)-N-[[3-[3-fluoro-4-(1-piperazinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (0.354 g, 1.05 mmol), and 1:1 tetrahydrofuran/dichloromethane (50 mL) at room temperature. After 3 days the reaction mixture was filtered to remove the precipitated 1,3-dicyclohexylurea and the filtrate concentrated in vacuo. The crude product was chromatographed over silica gel (20 g), eluting with a gradient of 1-6% methanol/chloroform, to give 0.446 g (95%) of the title compound as a white solid with mp 209°-210° C. ##STR14##

후처리

  1. distillationfollowed by distillation, saponification (1N aqueous sodium hydroxide, tetrahydrofuran, reflux), neutralization (1N HCl) and lyophilization
  2. filtrationAfter 3 days the reaction mixture was filtered
  3. customto remove the precipitated 1,3-dicyclohexylurea
  4. concentrationthe filtrate concentrated in vacuo
  5. customThe crude product was chromatographed over silica gel (20 g)
  6. washeluting with a gradient of 1-6% methanol/chloroform

출처 및 근거

ORD 기록
ord-7f8ebe493f5d4697b553881a9f4c9a97
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05700799

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