N,N'-Dimethylethylenediamine → (R)-4-[4-(4-benzoyloxymethyl-2-oxooxazolidin-3-yl)-3-fluoro-benzoyl]piperazine-1-carboxylic acid tert-butyl ester

HRID 1804038Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1804038
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:23])[C:15]2[CH:20]=[CH:19][C:18](Br)=[C:17]([F:22])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:24]=[C:25]1[NH:29][C@H:28]([CH2:30][O:31][C:32](=[O:39])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:27][O:26]1.C(=O)([O-])[O-].[K+].[K+].CNCCNC.[Cl-].[NH4+]>[Cu]I.C(OCC)(=O)C.C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:23])[C:15]2[CH:20]=[CH:19][C:18]([N:29]3[C@H:28]([CH2:30][O:31][C:32](=[O:39])[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH2:27][O:26][C:25]3=[O:24])=[C:17]([F:22])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

9

Edukt 5

HCID 8070N,N'-Dimethylethylenediamine2×HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 16213752(4S)-4-(Benzoyloxymethyl)oxazolidine-2-oneHCID 58484677tert-Butyl 4-[(4-bromo-3-fluorophenyl)carbonyl]piperazine-1-carboxylate

Produkt 1

HCID 54755120(R)-4-[4-(4-benzoyloxymethyl-2-oxooxazolidin-3-yl)-3-fluoro-benzoyl]piperazine-1-carboxylic acid tert-butyl esterAusbeute 31,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Katalysator2×HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of 4-(4-bromo-3-fluorobenzoyl)piperazine-1-carboxylic acid tert-butyl ester (3.49 g) described in Preparation Example 90, benzoic acid (R)-2-oxooxazolidin-4-ylmethyl ester (1.99 g), potassium carbonate (2.49 g) and copper (I) iodide (343 mg) were added toluene (18 mL) and N,N′-dimethylethylenediamine (387 μL), and the mixture was refluxed for 3 hr. Since the starting materials were left, copper (I) iodide (343 mg) and N,N′-dimethylethylenediamine (387 μL) were added and the mixture was further refluxed for 4 hr. The reaction mixture was cooled, ethyl acetate and aqueous ammonium chloride solution were added and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with a 1:1 mixture of saturated aqueous ammonium chloride solution and ammonia water, and the mixture was washed once with saturated aqueous ammonium chloride solution, once with saturated aqueous sodium chloride solution, and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography (chloroform:methanol) to give the title compound (1.48 g).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 3 hr
  2. waitSince the starting materials were left
  3. temperaturethe mixture was further refluxed for 4 hr
  4. temperatureThe reaction mixture was cooled
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with a 1:1 mixture of saturated aqueous ammonium chloride solution and ammonia water
  7. washthe mixture was washed once with saturated aqueous ammonium chloride solution, once with saturated aqueous sodium chloride solution
  8. dry with materialdried over sodium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customThe residue was purified by column chromatography (chloroform:methanol)

Quellen und Nachweise

ORD-Eintrag
ord-31044c418c0648eda16d8a68fb03827b
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354401B2

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