Acetic Acid → (2R,3R,4S,5R)-2-[2-[(Cyclohexylamino)methyl]-6-(phenethylamino)-9H-purin-9-yl]-5-(methoxymethyl)tetrahydro-3,4-furandiol

HRID 2268394Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2268394
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:15][CH2:16][C:17]1[N:25]=[C:24]2[C:20]([N:21]=[CH:22][N:23]2[C@H:26]2[C@H:30]([OH:31])[C@H:29]([OH:32])[C@@H:28]([CH2:33][O:34][CH3:35])[O:27]2)=[C:19]([NH:36][CH2:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[N:18]=1.C(O)(=O)C.[C:49]1(=O)[CH2:54][CH2:53][CH2:52][CH2:51][CH2:50]1>>[CH:49]1([NH:15][CH2:16][C:17]2[N:25]=[C:24]3[C:20]([N:21]=[CH:22][N:23]3[C@H:26]3[C@H:30]([OH:31])[C@H:29]([OH:32])[C@@H:28]([CH2:33][O:34][CH3:35])[O:27]3)=[C:19]([NH:36][CH2:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[N:18]=2)[CH2:54][CH2:53][CH2:52][CH2:51][CH2:50]1

Komponenten

5

Edukt 4

HCID 176Acetic AcidHCID 7967CyclohexanoneHCID 5049666Sodium triacetoxyborohydrideHCID 59975306(2R,3R,4S,5R)-2-[2-(aminomethyl)-6-(phenethylamino)-9H-purin-9-yl]-5-(methoxymethyl)tetrahydro-3,4-furandiol

Produkt 1

HCID 59975339(2R,3R,4S,5R)-2-[2-[(Cyclohexylamino)methyl]-6-(phenethylamino)-9H-purin-9-yl]-5-(methoxymethyl)tetrahydro-3,4-furandiolAusbeute 48,2 %

Versuchsvorschrift

Sodium triacetoxyborohydride (154 mg, 0.72 mmol) was added to a stirred solution of (2R,3R,4S,5R)-2-[2-(aminomethyl)-6-(phenethylamino)-9H-purin-9-yl]-5-(methoxymethyl)tetrahydro-3,4-furandiol (200 mg, 0.48 mmol) (preparation 48), acetic acid (30 mg, 0.48 mmol) and cyclohexanone (45 mg, 0.46 mmol). The reaction mixture was stirred for 24 hr at room temperature and the solvent then removed under reduced pressure. The residue was then azeotroped with dichloromethane before purification by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol:ammonia (93:7:0.3) to give the title compound (110 mg) as a viscous oil. MS: 497 (MH+).

Aufarbeitung

  1. customthe solvent then removed under reduced pressure
  2. customThe residue was then azeotroped with dichloromethane before purification by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol:ammonia (93:7:0.3)

Quellen und Nachweise

ORD-Eintrag
ord-9fe10f1aa1cd45829697c2602e771f26
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06326359B1

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