Sodium Iodide → (S)-isopropyl 2-(((S)-(((2R,3R,4R,5R)-5-(2-amino-6-oxo-1H-purin-9(6H)-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

HRID 537083노트

반응식

[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:15][C@H:14]([CH2:16][O:17][P@@:18]([NH:27][C@@H:28]([CH3:35])[C:29]([O:31][CH:32]([CH3:34])[CH3:33])=[O:30])([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:19])[C@@H:13]([OH:36])[C@:12]2([OH:38])[CH3:37])=[C:4]([O:39]C)[N:3]=1.O.O.O.O.O.O.O.[Cl-].[Ce+3].[Cl-].[Cl-].[I-].[Na+]>>[NH2:1][C:2]1[NH:3][C:4](=[O:39])[C:5]2[N:6]=[CH:7][N:8]([C@@H:11]3[O:15][C@H:14]([CH2:16][O:17][P@@:18]([NH:27][C@@H:28]([CH3:35])[C:29]([O:31][CH:32]([CH3:34])[CH3:33])=[O:30])([O:20][C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)=[O:19])[C@@H:13]([OH:36])[C@:12]3([OH:38])[CH3:37])[C:9]=2[N:10]=1

참가 물질

반응물 3

HCID 5238Sodium Iodide

HCID 21585214Cerium trichloride heptahydrate

HCID 67441510(S)-isopropyl 2-(((S)-(((2R,3R,4R,5R)-5-(2-amino-6-methoxy-9H-purin-9-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

생성물 1

HCID 136360910(S)-isopropyl 2-(((S)-(((2R,3R,4R,5R)-5-(2-amino-6-oxo-1H-purin-9(6H)-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate수율 35%

반응 조건

온도: 85 °C

실험 절차

To a stirred solution of 133 (160 mg, 0.28 mmol) was added cerium(III)chloride heptahydrate (154 mg, 0.414 mmol) and sodium iodide (41 mg, 0.276 mmol) at room temperature (21° C.). The mixture was heated at 85° C. for 6 h. The solvent was evaporated and the residue was chromatographed using 0-15% methanol/dichloromethane gradient to give pure product 134 as a white solid (55 mg, 35% yield).

후처리

customThe solvent was evaporated
customthe residue was chromatographed

출처 및 근거

ORD 기록: ord-cd0454b1ba6947c3a4051c7e21762d11
출처 데이터셋: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08859756B2

반응 노트

불러오는 중…