Hydrochloric Acid → 9-[4-(Diethoxyphosphorylmethoxy)-1-hydroxybut-2-oxy]guanine

HRID 345087노트

반응식

HRID 345087 반응식
C(OC([N:8](C(OC(C)(C)C)=O)[C:9]1[N:17]=[C:16]2[C:12]([N:13]=[CH:14][N:15]2[O:18][CH:19]([CH2:29][CH2:30][O:31][CH2:32][P:33]([O:38][CH2:39][CH3:40])([O:35][CH2:36][CH3:37])=[O:34])[CH2:20][O:21][Si](C(C)(C)C)(C)C)=[C:11]([O:41]C)[N:10]=1)=O)(C)(C)C.Cl>C(O)C>[CH2:36]([O:35][P:33]([CH2:32][O:31][CH2:30][CH2:29][CH:19]([O:18][N:15]1[CH:14]=[N:13][C:12]2[C:11](=[O:41])[NH:10][C:9]([NH2:8])=[N:17][C:16]1=2)[CH2:20][OH:21])([O:38][CH2:39][CH3:40])=[O:34])[CH3:37]

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 199935582-[Bis(t-butoxycarbonyl)amino]-9-[1-(t-butyldimethylsilyloxy)-4-(diethoxyphosphorylmethoxy)but-2-oxy]-6-methoxypurine

생성물 1

HCID 1363411999-[4-(Diethoxyphosphorylmethoxy)-1-hydroxybut-2-oxy]guanine수율 48%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of 2-[bis(t-butoxycarbonyl)amino]-9-[1-(t-butyldimethylsilyloxy)-4-(diethoxyphosphorylmethoxy)but-2-oxy]-6-methoxypurine (415 mg, 0.57 mmol) was dissolved in ethanol (5 ml) and 5M hydrochloric acid (0.6 ml) and heated under reflux for 3.5 h. The reaction was evaporated in vacuo and the residue chromatographed on silica, eluting with chloroform-methanol 10:1, affording 9-[4-(diethoxyphosphorylmethoxy)-1-hydroxybut-2-oxy]guanine (110 mg, 48%) as a pale tan solid. νmax (KBr) 3400, 1680, 1640 and 1600 cm-1 ; δH [(CD3)2SO] 1.22 (6H, t, J7.1 Hz, 2×CH2CH3), 1.91 (2H, m, CHCH2CH2O), 3.54 (2H, m, CH2OH), 3.74 (2H, m, CH2OCH2P), 3.85 (2H, d, J8.2 Hz, CH2P), 4.03 (4H, m, 2×CH2CH3), 4.30 (1H, m, HOCH2CH), 5.01 (1H, m, D2O exchangeable OH), 6.65 (2H, br.s, D2O exchangeable, NH2); m/z (FAB+ve Ion), 428 (MNa+), 406 (MH+).

후처리

  1. temperatureunder reflux for 3.5 h
  2. customThe reaction was evaporated in vacuo
  3. customthe residue chromatographed on silica
  4. washeluting with chloroform-methanol 10:1

출처 및 근거

ORD 기록
ord-029d4490a18246e8a7885b05333a6b31
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05055458

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