Ammonia → 5-Fluoro-2'-O-methyluridine

HRID 2210629ノート

反応式

HRID 2210629 の反応式
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]

参加物

4

反応物 2

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

生成物 1

HCID 217323735-Fluoro-2'-O-methyluridine収率 98%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-609fcb5709f64136b1c8d23cf9f89029
出典データセット
uspto-grants-1995_10
特許番号
US05459243

反応ノート

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