Water → 6-hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylic acid cyclohexylamide

HRID 19555

Reaktionsgleichung

Reaktionsgleichung von HRID 19555
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:7]([C:12]([OH:14])=O)[C:8]2=[O:11])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:28]1([NH2:34])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.O>ClCCl>[CH:28]1([NH:34][C:12]([C:7]2[C:8](=[O:11])[C:9]3[C:5]([C:6]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:4][CH:3]=[C:2]([OH:1])[CH:10]=3)=[O:14])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7965CyclohexylamineHCID 8471TriethylamineHCID 686989826-hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylic acid

Produkt 1

HCID 686971666-hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylic acid cyclohexylamideAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

6-Hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylic acid (100 mg, 0.38 mmol) obtained in Step 2 was dissolved in dichloromethane, and triethylamine (175 μl, 1.25 mmol) and cyclohexylamine (43 μl, 0.38 mmol) were added thereto at 10° C. Then, bis(2-oxo-3-oxazoline)phosphoryl chloride (100 mg, 0.38 mmol) was further added thereto, stirred for 10˜20 minutes at RT, and then stirred for additional 1 hr in a water bath. After water was added to complete the reaction, the mixture washed with sodium bicarbonate and extracted with dichloromethane. The organic layer was separated, dried over anhydrous MgSO4, concentrated under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 26 mg of the titled compound (yield: 20.0%) as a red solid.

Aufarbeitung

  1. customat 10° C
  2. stirringstirred for additional 1 hr in a water bath
  3. customthe reaction
  4. washthe mixture washed with sodium bicarbonate
  5. extractionextracted with dichloromethane
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous MgSO4
  8. concentrationconcentrated under a reduced pressure
  9. customThe resulting residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-41523592252d464e85fe5b4db700fe11
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745439B2

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