Sodium Hydroxide → 2-Hydroxyabacavir

HRID 2393964Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2393964
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@H:11]2[CH2:15][C@H:14]([OH:16])[C@@H:13]([CH2:17][OH:18])[CH2:12]2)=[C:4](Cl)[N:3]=1.[CH:20]1([NH2:23])[CH2:22][CH2:21]1.[OH-].[Na+]>C(O)C>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@H:11]2[CH2:15][C@H:14]([OH:16])[C@@H:13]([CH2:17][OH:18])[CH2:12]2)=[C:4]([NH:23][CH:20]2[CH2:22][CH2:21]2)[N:3]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 69828CyclopropylamineHCID 11108834HCID 11108834, Verbindung

Produkt 1

HCID 99484072-Hydroxyabacavir

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

(+)-(1S, 2R, 4R)-4-(2-Amino-6chloro-9H-purin-9-yl)-2-(hydroxymethyl)cyclopentanol (425 mg, 1.5 mmol), cyclopropylamine (Aldrich, 1.4 mL), and ethanol (4 mL) were refluxed for 3 hours. To the cooled solution was added 1N sodium hydroxide (1.5 mL). The residual oil left on evaporation of volatiles under vacuum was chromatographed on silica gel. Title compound was eluted with methanol: ethyl acetate/15:85 as a white solid foam which solidified to white powder in methanol-acetonitrile (309 mg, 68%); m.p. 174°-176° C.; mass spectrum (Cl, CH4) 305 (M+1); 1H-NMR (DMSO-d6) δ: 7.79 (s, 1, H-8); 7.25 (d, J=2.9 Hz, 1, NH), 5.79 (s, 2, NH2), 4.90-4.75 (m, 1, CH--N), 4.73 (d, J=4.0 Hz, 1, OH), 4.63 (t, J=5.3 Hz, 1, CHOH), 4.08-4.00 (m, 1, CHO), 3.58-3.38 (m, 2, CH2O), 3.05-2.95 (m, 1, CH--NH), 2.35-2.20 (m. 1, CH), 2.18-2.0 (m, 1, 1/2CH2), 2.0-1.9 (m, 2, methylene), 1.7-1.5 (m, 1, 1/2CH2), 0.70-0.50 (m, 4, 2CH2 of cyclopropyl); [α]20589 +7.72°, [α]20578 +7.87°, [α]20546 +8.77°, [α]20436 +14.4°, [α]20365 +20.1° (c=0.66, methanol).

Aufarbeitung

  1. waitThe residual oil left on evaporation of volatiles under vacuum
  2. customwas chromatographed on silica gel
  3. washTitle compound was eluted with methanol

Quellen und Nachweise

ORD-Eintrag
ord-51bb360c98684e88a7ab6df11cab14e1
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05808147

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