Propyne → (r)-Cyclopropanecarboxylic acid[9-(3-fluoro-benzyl)-6-(5-methyl-isoxazol-3-yl)-2,3,4,9-tetrahydro-1h-carbazol-3-yl]-amide

HRID 545581Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 545581
[CH:1]#[C:2][CH3:3].[F:4][C:5]1[CH:6]=[C:7]([CH:31]=[CH:32][CH:33]=1)[CH2:8][N:9]1[C:21]2[CH2:20][CH2:19][C@@H:18]([NH:22][C:23]([CH:25]3[CH2:27][CH2:26]3)=[O:24])[CH2:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[C:13]([CH:28]=[N:29][OH:30])[CH:14]=2>C(Cl)Cl.[O-]Cl.[Na+]>[F:4][C:5]1[CH:6]=[C:7]([CH:31]=[CH:32][CH:33]=1)[CH2:8][N:9]1[C:21]2[CH2:20][CH2:19][C@@H:18]([NH:22][C:23]([CH:25]3[CH2:27][CH2:26]3)=[O:24])[CH2:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[C:13]([C:28]1[CH:1]=[C:2]([CH3:3])[O:30][N:29]=1)[CH:14]=2

Komponenten

5

Edukt 2

HCID 6335PropyneHCID 87305657(r)-Cyclopropanecarboxylic acid[9-(3-fluoro-benzyl)-6-(hydroxyimino-methyl)-2,3,4,9-tetrahydro-1h-carbazol-3-yl]-amide

Produkt 1

HCID 59161297(r)-Cyclopropanecarboxylic acid[9-(3-fluoro-benzyl)-6-(5-methyl-isoxazol-3-yl)-2,3,4,9-tetrahydro-1h-carbazol-3-yl]-amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 23665760Sodium HypochloriteLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

Bubble propyne gas through a solution of (R)-cyclopropanecarboxylic acid[9-(3-fluoro-benzyl)-6-(hydroxyimino-methyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-amide (Example 203) (0.065 g, 0.16 mmol) in methylene chloride and NaOCl solution maintained in a sealed tube. Cap the tube and stir at 23° C. for 16 h. Partition the reaction between methylene chloride and water. Separate and dry the organic portion over Na2SO4 to give 0.045 g of a tan solid. Purify by silca gel chromatography, eluting with 20-80% EtOAc/gradient to give an 0.030g (42%) of an off-white solid. mp: 190-192° C.; MS (ES): m/z 444 (M+1).

Aufarbeitung

  1. temperaturemaintained in a sealed tube
  2. customCap the tube
  3. customPartition
  4. customthe reaction between methylene chloride and water
  5. customSeparate
  6. dry with materialdry the organic portion over Na2SO4

Quellen und Nachweise

ORD-Eintrag
ord-e242ecea617240a88b1166e9f019eb15
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935722B2

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