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

HRID 1276441
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1276441
[O:1]1[C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=[N:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[O:21]=[C:22]1[N:26]([C:27]2[CH:32]=[CH:31][C:30]([CH:33]3[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)=[C:29]([F:39])[CH:28]=2)[CH2:25][C@H:24]([CH2:40][NH:41][C:42](=[O:44])[CH3:43])[O:23]1>O1CCCC1>[O:1]1[C:5]([C:6]([N:36]2[CH2:37][CH2:38][CH:33]([C:30]3[CH:31]=[CH:32][C:27]([N:26]4[CH2:25][C@H:24]([CH2:40][NH:41][C:42](=[O:44])[CH3:43])[O:23][C:22]4=[O:21])=[CH:28][C:29]=3[F:39])[CH2:34][CH2:35]2)=[O:8])=[CH:4][CH:3]=[N:2]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 20605991,2-Oxazole-5-carboxylic acidHCID 15887422(S)-(-)-N-[[2-Oxo-3-[4-(4-piperidinyl)-3-fluorophenyl]-5-oxazolidinyl]methyl]acetamide

Produkt 1

HCID 53880492(S)-(-)-N-[[3-[4-[1-(Isoxazole-5-carbonyl)-4-piperidinyl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

A solution of isoxazole-5-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 290-292° 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-144665fe2b91448c90d675cf9fffd5b2
Quelldatensatz
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06166056

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