Dicyclohexylcarbodiimide → HCID 15345486, Verbindung

HRID 1456881Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1456881
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][S:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]2[O:17][C:16]([C:18]([OH:20])=O)=[CH:15][C:14]=2[CH:21]=1.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:37][C:38]1[CH:39]=[C:40]2[C:44](=[CH:45][CH:46]=1)[NH:43][C:42]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])=[CH:41]2>C1COCC1.C(Cl)Cl.CN(C)C1C=CN=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][S:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]2[O:17][C:16]([C:18]([NH:37][C:38]3[CH:39]=[C:40]4[C:44](=[CH:45][CH:46]=3)[NH:43][C:42]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])=[CH:41]4)=[O:20])=[CH:15][C:14]=2[CH:21]=1

Komponenten

7

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 10633339Tert-butyl 5-amino-1H-indole-2-carboxylateHCID 153454855-(2-Pyridyldithiomethyl)benzofuran-2-carboxylic acid

Produkt 1

HCID 15345486HCID 15345486, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel3×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A stirred solution of 15 (247 mg, 0.78 mmol) in 30 mL dry THF at room temperature under argon, was treated sequentially with solutions of dicyclohexylcarbodiimide (177 mg, 0.86 mmol) in 5 mL methylene chloride, 4-(dimethylamino)-pyridine (29 mg, 0.23 mmol) in 2 mL methylene chloride, and 10 (200 mg, 0.86 mmol) in 5 mL methylene chloride. The reaction mixture was stirred overnight. Dicyclohexylurea was filtered from the reaction mixture, and the filtrate was washed with water, cold 0.1M HCl, saturated aqueous sodium bicarbonate, and water. The organic solution was dried over magnesium sulfate, filtered, and concentrated to give a dark oil. The crude product was further purified by chromatography on a silica gel column, eluting with ethyl acetate:hexanes to give 16 as an off-white solid: NMR (acetone-d6) δ1.6 (s, 9H), δ4.3 (s, 2H), δ7.0-8.6 (m, 12H).

Aufarbeitung

  1. filtrationDicyclohexylurea was filtered from the reaction mixture
  2. washthe filtrate was washed with water, cold 0.1M HCl, saturated aqueous sodium bicarbonate, and water
  3. dry with materialThe organic solution was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a dark oil
  7. customThe crude product was further purified by chromatography on a silica gel column
  8. washeluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-b603aabed65f45fbad509dc4a9dbbfe9
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05846545

Notizen zur Reaktion

Wird geladen…