Acetic Acid → HCID 22876311, Verbindung

HRID 1376480

Reaktionsgleichung

Reaktionsgleichung von HRID 1376480
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=1.[H-].[Na+].[C:21]([O:24][CH2:25][C@@H:26]1[CH2:31][CH:30]=[CH:29][CH2:28][C@@H:27]1[CH2:32]Br)(=[O:23])[CH3:22].C(O)(=O)C>CN(C=O)C>[C:21]([O:24][CH2:25][C@@H:26]1[CH2:31][CH:30]=[CH:29][CH2:28][C@@H:27]1[CH2:32][N:8]1[CH:7]=[N:6][C:5]2[C:9]1=[N:10][C:2]([NH2:1])=[N:3][C:4]=2[O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)(=[O:23])[CH3:22]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 45786-(Phenylmethoxy)-9H-purin-2-amineHCID 24758Sodium hydrideHCID 23255906HCID 23255906, Verbindung

Produkt 1

HCID 22876311HCID 22876311, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a suspension of 2-amino-6-benzyloxypurine (1 mmol) in DMF (2 mL) was added sodium hydride (1.15 eq) and the mixture stirred at room temperature for 30 minutes. A solution of 1(R)-acetoxymethyl-2(S)-bromomethylcyclohex-4-ene (1.1 eq) in DMF (0.75 mL) and the reaction stirred at 60° C. for 16 hours. The reaction was neutralized with acetic acid and concentrated. The desired compound was purified by silica gel chromatography (chloroform:methanol 95:5) as a colorless foam. 1HNMR (500 mHz, CDCl3): 8.02 ppm (s, 1H); 7.65 (s, 1H); 7.49 (d, 2H); 7.38-7.26 (m, 3H); 5.65 (dd, 2H); 5.56 (s, 2H); 4.33 (dd, 1H); 4.12 (dd, 1H); 4.06-3.97 (m, 2H); 2.40 (bs, 1H); 2.23-1.75 (m, 6H); 2.20 (s, 3H).

Aufarbeitung

  1. concentrationconcentrated
  2. customThe desired compound was purified by silica gel chromatography (chloroform:methanol 95:5) as a colorless foam

Quellen und Nachweise

ORD-Eintrag
ord-c499139d8bee4ad0946870c5742e064d
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05663175

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