Hexamethyldisilazane → (2R,3R,4R,5R)-4-(Benzoyloxy)-5-[2-cyano-6-(phenethylamino)-9H-purin-9-yl]-2-(methoxymethyl)tetrahydro-3-furanyl benzoate

HRID 2268431ノート

反応式

HRID 2268431 の反応式
[CH2:1]([NH:9][C:10]1[N:18]=[C:17]([C:19]#[N:20])[N:16]=[C:15]2[C:11]=1[N:12]=[CH:13][NH:14]2)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:21]([O:29][C@H:30]1[C@@H:34]([O:35][C:36](=[O:43])[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C@H:33](OC(=O)C)[O:32][C@@H:31]1[CH2:48][O:49][CH3:50])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(O[C@H]1[C@@H](OC(=O)C2C=CC=CC=2)[C@@H](OC(=O)C)O[C@@H]1COC)(=O)C1C=CC=CC=1.S([O-])([O-])(=O)=O.[NH4+].[NH4+].C[Si](C)(C)N[Si](C)(C)C.Br[Si](C)(C)C>[Bi](Br)(Br)Br.ClCCl.C(#N)C>[C:21]([O:29][C@H:30]1[C@@H:34]([O:35][C:36](=[O:43])[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C@H:33]([N:14]2[CH:13]=[N:12][C:11]3[C:15]2=[N:16][C:17]([C:19]#[N:20])=[N:18][C:10]=3[NH:9][CH2:1][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[O:32][C@@H:31]1[CH2:48][O:49][CH3:50])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

10

反応物 6

HCID 13838HexamethyldisilazaneHCID 76113BromotrimethylsilaneHCID 6097028Ammonium SulfateHCID 69534087(2R,3R,4R,5R)-5-(acetyloxy)-4-(benzoyloxy)-2-(methoxymethyl)tetrahydro-3-furanyl benzoateHCID 69534095(2R,3R,4R,5S)-5-(acetyloxy)-4-(benzoyloxy)-2-(methoxymethyl)tetrahydro-3-furanyl benzoateHCID 178510600HCID 178510600、化合物

生成物 1

HCID 59975283(2R,3R,4R,5R)-4-(Benzoyloxy)-5-[2-cyano-6-(phenethylamino)-9H-purin-9-yl]-2-(methoxymethyl)tetrahydro-3-furanyl benzoate

試薬・触媒・溶媒 3

HCID 82232bismuth(III) bromide触媒HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

実験手順

The title compound was prepared by a similar method to preparation 11 using 6-(phenethylamino)-9H-purine-2-carbonitrile (3.8 g, 11.2 mmol) (preparation 45), (2R,3R,4R,5S)-5-(acetyloxy)-4-(benzoyloxy)-2-(methoxymethyl)tetrahydro-3-furanyl benzoate and (2R,3R,4R,5R)-5-(acetyloxy)-4-(benzoyloxy)-2-(methoxymethyl)tetrahydro-3-furanyl benzoate (preparation 4) (6 g, 14.5 mmol), ammonium sulfate (200 mg, 1.2 mmol), 1,1,1,3,3,3-hexamethyidisilazane (150 ml), bromotrimethylsilane (8 ml, 177 mmol), acetonitrile (80 ml), dichloromethane (80 ml) and bismuth tribromide (0.35 g, 0.24 mmol). The product was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol (99.5:0.5). This gave the title compound (7.9 g) as a white foam. MS: 619 (MH+).

後処理

  1. customThe product was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol (99.5:0.5)

出典と根拠

ORDレコード
ord-d0161171eeee41c795f891434c6eb1cc
出典データセット
uspto-grants-2001_12
特許番号
US06326359B1

反応ノート

読み込み中…