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

HRID 1708100노트

반응식

HRID 1708100 반응식
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]

참가 물질

4

반응물 2

HCID 76113BromotrimethylsilaneHCID 10088675HCID 10088675, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-eeda8d0c4855473ab7781af81b6d8776
출처 데이터셋
uspto-grants-1994_10
특허 번호
US05356886

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