1,1'-Carbonyldiimidazole → (S)-(-)-N-[[3-[4-[1-(Indole-2-carbonyl)-4-piperidinyl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

HRID 277797Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 277797
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[O:25]=[C:26]1[N:30]([C:31]2[CH:36]=[CH:35][C:34]([CH:37]3[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]3)=[C:33]([F:43])[CH:32]=2)[CH2:29][C@H:28]([CH2:44][NH:45][C:46](=[O:48])[CH3:47])[O:27]1>O1CCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([N:40]1[CH2:41][CH2:42][CH:37]([C:34]2[CH:35]=[CH:36][C:31]([N:30]3[CH2:29][C@H:28]([CH2:44][NH:45][C:46](=[O:48])[CH3:47])[O:27][C:26]3=[O:25])=[CH:32][C:33]=2[F:43])[CH2:38][CH2:39]1)=[O:12]

Komponenten

5

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 72899Indole-2-carboxylic acidHCID 15887422(S)-(-)-N-[[2-Oxo-3-[4-(4-piperidinyl)-3-fluorophenyl]-5-oxazolidinyl]methyl]acetamide

Produkt 1

HCID 54177616(S)-(-)-N-[[3-[4-[1-(Indole-2-carbonyl)-4-piperidinyl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of indole-2-carboxylic acid (79 mg) and 1,1′-carbonyldiimidazole (80 mg) in dry tetrahydrofuran (2.0 mL) is stirred at ambient temperature for one hour, and a solution of (S)-(−)-N-[[2-oxo-3-[4-(4-piperidinyl)-3-fluorophenyl]-5-oxazolidinyl]methyl]acetamide (EXAMPLE 20, 150 mg) in dry tetrahydrofuran (6.0 mL) is added. The mixture is then stirred at ambient temperature for 19 hours, concentrated under reduced pressure, diluted with methylene chloride (20 mL), washed with saturated aqueous sodium bicarbonate (10 mL), water (10 mL) and saline (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product which is chromagraphed on silica gel (70-230 mesh, 10 g), eluting with methanol/methylene chloride (7.5/92.5). Pooling and concentration of those fractions with an Rf=0.67 by TLC (methanol/chloroform, 10/90) and recrystallization from chloroform/diethyl ether gives the title compound, mp 223-225° C.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. additiondiluted with methylene chloride (20 mL)
  3. washwashed with saturated aqueous sodium bicarbonate (10 mL), water (10 mL) and saline (10 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give the crude product which
  7. washeluting with methanol/methylene chloride (7.5/92.5)
  8. customPooling and concentration of those fractions with an Rf=0.67 by TLC (methanol/chloroform, 10/90) and recrystallization from chloroform/diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-5b175246e3e0400a95dc24a8f3761e99
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06358942B1

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