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

HRID 2268431노트

반응식

HRID 2268431 반응식
[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

참가 물질

10

반응물 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, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 82232bismuth(III) bromide촉매HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

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+).

후처리

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

출처 및 근거

ORD 기록
ord-d0161171eeee41c795f891434c6eb1cc
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06326359B1

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