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

HRID 1708091노트

반응식

HRID 1708091 반응식
C([O:4][P:5](/[CH:11]=[CH:12]/[CH2:13][CH2:14][O:15][N:16]1[CH:24]=[N:23][C:22]2[C:17]1=[N:18][CH:19]=[N:20][C:21]=2[NH2:25])([O:7]C(C)C)=[O:6])(C)C.Br[Si](C)(C)C>ClCCl>[P:5](/[CH:11]=[CH:12]/[CH2:13][CH2:14][O:15][N:16]1[CH:24]=[N:23][C:22]2[C:17]1=[N:18][CH:19]=[N:20][C:21]=2[NH2:25])([OH:6])([OH:7])=[O:4]

참가 물질

4

반응물 2

HCID 76113BromotrimethylsilaneHCID 10067662(E)-9-[4-(diisopropoxyphosphoryl)but-3-enyloxy]adenine

생성물 1

HCID 6474323[(E)-4-(6-aminopurin-9-yl)oxybut-1-enyl]phosphonic acid수율 84%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (E)-9-[4-(diisopropoxyphosphoryl)but-3-enyloxy]adenine (105 mg, 284 μmol) in dichloromethane was added bromotrimethylsilane (0.87 g, 5.68 mmol). The resulting white suspension was stirred at room temperature under dry nitrogen for 18 hr. The solution was evaporated to dryness and the residue azeotroped with methanol (×3). The residue was purified by column chromatography on reverse phase silica gel eluting with water to give (E)-9-(4-phosphonobut-3-enyloxy)adenine as a white solid (68 mg, 84%), m.p. 249°-251° C.; λmax (MeOH) 260 (11,985)nm; υmax (KBr) 3110, 2300, 1695, 1470, 1410, 1330 and 1030 cm-1 ; δH[(CD3)2SO] 2.62 (2H, m, CH2), 4.50 (2t, t, J 7 Hz, CH2O ), 5.94 (1H, dd, J 17 Hz and 22 Hz, PCH=CH), 6.50 (1H, ddt, J 6 Hz, 17 Hz and 22 Hz, PCH=CH), 7.39 (2H, br.s, NH2), 8.16 (1H, s, H-2/H-8), 8.35 (1H, s, H-2/H-8); FABMS (thioglycerol) 286 (MH+) (Found: C, 35.75; H, 4.00; N, 23.14; Br, 5.41%. C9H12N5O4P.0.2HBr requires C, 35.86; H, 4.08; N, 23.24; Br, 5.30%).

후처리

  1. customThe solution was evaporated to dryness
  2. customthe residue azeotroped with methanol (×3)
  3. customThe residue was purified by column chromatography on reverse phase silica gel eluting with water

출처 및 근거

ORD 기록
ord-f6d2aabe74ee4756b4a3b191f4c04e2c
출처 데이터셋
uspto-grants-1994_10
특허 번호
US05356886

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