Triphenylphosphine → HCID 11754512, 화합물

HRID 1708098

반응식

HRID 1708098 반응식
[OH:1][N:2]1[CH:10]=[N:9][C:8]2[C:3]1=[N:4][CH:5]=[N:6][C:7]=2[N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21].O[CH2:23][CH2:24]/[CH:25]=[CH:26]\[P:27](=[O:34])([O:31][CH2:32][CH3:33])[O:28][CH2:29][CH3:30].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH2:32]([O:31][P:27](/[CH:26]=[CH:25]\[CH2:24][CH2:23][O:1][N:2]1[CH:10]=[N:9][C:8]2[C:3]1=[N:4][CH:5]=[N:6][C:7]=2[N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21])([O:28][CH2:29][CH3:30])=[O:34])[CH3:33]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10081772HCID 10081772, 화합물HCID 145239709-Hydroxy-6-phthalimidopurine

생성물 1

HCID 11754512HCID 11754512, 화합물수율 60%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a mixture of 9-hydroxy-6-phthalimidopurine (320 mg, 1.14 mmol) , diethyl (Z)-4-hydroxybut-1-enylphosphonate (250 mg, 1.20 mmol) and triphenyl phosphine (448 mg, 1.71 mmol) in dry tetrahydrofuran (11 ml) stirred at 0° C. under dry nitrogen was added diethyl azodicarboxylate (296 mg, 170 mmol). The mixture was allowed to warm to r.t. and stirred for 2.3 hr. The solvent was removed and the residue was purified by column chromatography on silica gel eluting with acetone-hexane (1:1, 4:3) to give (Z)-9-[4-(diethoxyphosphoryl)but-3-enyloxy]-6-phthalimidopurine as a light brown gum (320 mg, 60%); λmax (EtOH) 271 (14,680)nm; υmax (KBr) 2980, 1735, 1595, 1575, 1360, 1330, 1245 and 1025 cm-1 ; δH [(CD3)2SO] 1.23 (6H, t, J 7 Hz, CH3), 3.05 (2H, m, CH2), 3.98 (4H, dq, J 7 Hz and 8Hz, CH2CH 3), 4.63 (2H, t, J 6 Hz, CH2O ), 5.90 (1H, dd, J 14 Hz and 20 Hz, PCH=CH), 6.75 (1H, ddt, J 7 Hz, 14 Hz and 52 Hz, PCH=CH), 8.05 (4H, m, C6H4), 9.05 (1H, s, H-2/H-8), 9.10 (1H, s, H-2/H-8) (Found: C, 53.77; H, 4.87; N, 14.52%; MH+ 472.1384. C21H22N5O6P requires C, 53.50; H, 4.70; N, 14.86%; MH+ 472.1386).

후처리

  1. temperatureto warm to r.t.
  2. stirringstirred for 2.3 hr
  3. customThe solvent was removed
  4. customthe residue was purified by column chromatography on silica gel eluting with acetone-hexane (1:1, 4:3)

출처 및 근거

ORD 기록
ord-2f7678df38634b6ab8fcf1b788e1e8a0
출처 데이터셋
uspto-grants-1994_10
특허 번호
US05356886

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