Bromotrimethylsilane → [(Z)-4-(6-aminopurin-9-yl)oxybut-1-enyl]phosphonic acid

HRID 1708100ノート

反応式

HRID 1708100 の反応式
C([O:3][P:4](/[CH:9]=[CH:10]\[CH2:11][CH2:12][O:13][N:14]1[CH:22]=[N:21][C:20]2[C:15]1=[N:16][CH:17]=[N:18][C:19]=2[NH2:23])([O:6]CC)=[O:5])C.Br[Si](C)(C)C>ClCCl>[P:4](/[CH:9]=[CH:10]\[CH2:11][CH2:12][O:13][N:14]1[CH:22]=[N:21][C:20]2[C:15]1=[N:16][CH:17]=[N:18][C:19]=2[NH2:23])([OH:5])([OH:6])=[O:3]

参加物

4

反応物 2

HCID 76113BromotrimethylsilaneHCID 10088675HCID 10088675、化合物

生成物 1

HCID 6474312[(Z)-4-(6-aminopurin-9-yl)oxybut-1-enyl]phosphonic acid収率 81%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (Z)-9-[4-(diethoxyphosphoryl)-but-3-enyloxy]adenine (145 mg, 425 μmol) in dichlormethane (10 ml) was added bromotrimethylsilane (1.29 g, 8.48 mmol) and the resulting solution was stirred at room temperature under dry nitrogen for 18 hr. The solvent was removed and the residue was azeotroped with methanol (×5). The residue was purified by column chromatography on reverse phase silica gel eluting with water to give (Z)-9-(4-phosphonobut-3-enyloxy]adenine as a white solid (98 mg, 81%), m.p. 238° C.; λmax (MeOH) 260 (13,515)nm; υmax (KBr) 3420, 3200, 3085, 2970, 1700, 1610, 1485, 1415 and 1335 cm-1 ; δH [(CD3)2SO] 2.94 (2H, m, CH2), 4.43 (2H, t, J 7 Hz, CH2O ), 5.77 (1H, dd, J 14 Hz and 17 Hz, PCH=CH), 6.40 (1H, ddt, J 7 Hz, 14 Hz and 47 Hz, PCH=CH), 7.40 (2H, br.s, NH2). 8.15 (1H, s, H-2/H-8), 8.42 (1H, s, H-2/H-8); FABMS (thioglycerol) 286 (NH+) (Found: C, 36.71; H, 4.16; N, 23.96%. C9H12N5O4P.0.4H20 requires C, 36.96; H, 4.41; N, 23.95%).

後処理

  1. customThe solvent was removed
  2. customthe residue was azeotroped with methanol (×5)
  3. customThe residue was purified by column chromatography on reverse phase silica gel eluting with water

出典と根拠

ORDレコード
ord-eeda8d0c4855473ab7781af81b6d8776
出典データセット
uspto-grants-1994_10
特許番号
US05356886

反応ノート

読み込み中…