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

反応式

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

参加物

反応物 4

HCID 176Acetic Acid

HCID 7967Cyclohexanone

HCID 5049666Sodium triacetoxyborohydride

HCID 59975306(2R,3R,4S,5R)-2-[2-(aminomethyl)-6-(phenethylamino)-9H-purin-9-yl]-5-(methoxymethyl)tetrahydro-3,4-furandiol

生成物 1

HCID 59975339(2R,3R,4S,5R)-2-[2-[(Cyclohexylamino)methyl]-6-(phenethylamino)-9H-purin-9-yl]-5-(methoxymethyl)tetrahydro-3,4-furandiol収率 48.2%

実験手順

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+).

後処理

customthe solvent then removed under reduced pressure
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)

出典と根拠

ORDレコード: ord-9fe10f1aa1cd45829697c2602e771f26
出典データセット: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US06326359B1

反応ノート

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