Phthalimide → HCID 69417417, Verbindung

HRID 1374071

Reaktionsgleichung

Reaktionsgleichung von HRID 1374071
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:20]1(=[O:30])[NH:24][C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12.[C:31]([NH:39][C:40]1[C:41]2[N:42]=[CH:43][N:44]([C:53]=2[N:54]=[CH:55][N:56]=1)[C@@H:45]1[O:52][C@H:49]([CH2:50]O)[C@@H:47]([OH:48])[CH2:46]1)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1.ClCCl>[C:20]1(=[O:30])[N:24]([CH2:50][C@H:49]2[O:52][C@@H:45]([N:44]3[C:53]4[N:54]=[CH:55][N:56]=[C:40]([NH:39][C:31](=[O:38])[C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)[C:41]=4[N:42]=[CH:43]3)[CH2:46][C@@H:47]2[OH:48])[C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12

Komponenten

7

Edukt 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 107558N-benzoyl-2'-deoxyadenosine

Produkt 1

HCID 69417417HCID 69417417, VerbindungAusbeute 30,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 13.11 g (50 mmol) Ph3P, 6.99 g (47.5 mmol) phthalimide and 17.77 g (50 mmol) N6-benzoyl-2′-deoxyadenosine in 400 mL dry THF was added 9.84 mL (50 mmol) of diisopropyl azodicarboxylate under a nitrogen atmosphere. The resulting mixture was stirred for 2 h in an ice water bath and then 4 h at room temperature. After most of the THF was evaporated under reduced pressure, the oily residue was added 100 ml of dichloromethane. The precipitate, which was formed after the addition of dichloromethane, was filtered and washed with small amounts of THF/dichloromethane mixture (1:1). The filtrate was concentrated and purified with a silica gel column chromatography (dichloromethane/THF=2:1 then dichloromethane/methanol=19:1) to give 7.1 g of compound 2.

Aufarbeitung

  1. custom4 h
  2. customat room temperature
  3. customAfter most of the THF was evaporated under reduced pressure
  4. additionthe oily residue was added 100 ml of dichloromethane
  5. customThe precipitate, which was formed
  6. filtrationwas filtered
  7. washwashed with small amounts of THF/dichloromethane mixture (1:1)
  8. concentrationThe filtrate was concentrated
  9. custompurified with a silica gel column chromatography (dichloromethane/THF=2:1

Quellen und Nachweise

ORD-Eintrag
ord-8891f53e7a104fb595b49ea395a65130
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07164014B2

Verknüpfte Notizen

Wird geladen…