Ammonia → 5-Fluoro-2'-O-methyluridine

HRID 2210629노트

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HRID 2210629 반응식
C([O:9][C@@H:10]1[C@@H:14]([CH2:15][O:16]C(=O)C2C=CC=CC=2)[O:13][C@@H:12]([N:25]2[CH:32]=[C:31]([F:33])[C:29](=[O:30])[NH:28][C:26]2=[O:27])[C@@H:11]1[O:34][CH3:35])(=O)C1C=CC=CC=1.N>CO>[CH3:35][O:34][C@@H:11]1[C@H:10]([OH:9])[C@@H:14]([CH2:15][OH:16])[O:13][C@H:12]1[N:25]1[CH:32]=[C:31]([F:33])[C:29](=[O:30])[NH:28][C:26]1=[O:27]

참가 물질

4

반응물 2

HCID 222AmmoniaHCID 100055463',5'-Di-O-benzoyl-5-fluoro-2'-O-methyluridine

생성물 1

HCID 217323735-Fluoro-2'-O-methyluridine수율 98%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

3',5'-Di-O-benzoyl-2'-O-methyl-5-fluorouridine (9.6 g, 20 mmoles) was dissolved in methanol (350 ml) which had been previously saturated with ammonia at -20° C. The solution was sealed in a stainless steel bomb at room temperature for 17 hours and then concentrated to an oil under reduced pressure. The oil was chromatographed on silica gel (200 g) using ethyl acetate to give 5.4 g (98%) of 2'-O-methyl-5-fluorouridine as a white solid. A portion (0.5 g) was crystallized from ethyl acetate/toluene to yield 0.4 g of white needles as the analytical sample, mp 151°-152° C. (lit. M. J. Robins, et. al., J. Am. Chem. Soc., 89, 7381 (1976)., mp 144°-147° C.). 1H NMR (DMSO-d6): δ 3.39 (s, 3H, OCH3), 3.5-3.7 (m, 2H, H-5'), 3.7-3.9 (m, 2H, H-3',4'), 4.13 (m, 1H, H-2'), 5.18 (d, J=6 Hz, 1H, 3'--OH), 5.35 (br t, 1H, 5'--OH), 5.81 (dd, 1H, H-1'), 8.35 (d, J=7 Hz, 1H, H-6), 11.40 (br d, 1H, N--H). Anal. Calcd for C10H13N2O6 (276.22): C, 43.48; H, 4.74; N, 10.14. Found: C, 43.56; H, 4.63; N, 10.02.

후처리

  1. concentrationconcentrated to an oil under reduced pressure
  2. customThe oil was chromatographed on silica gel (200 g)

출처 및 근거

ORD 기록
ord-609fcb5709f64136b1c8d23cf9f89029
출처 데이터셋
uspto-grants-1995_10
특허 번호
US05459243

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