Isopropanol → 1-beta-L-Ribofuranosyl-6-methyluracil

HRID 478771ノート

反応式

HRID 478771 の反応式
C([O:9][C@H:10]1[C@@H:14]([O:15]C(=O)C2C=CC=CC=2)[C@H:13]([CH2:24][O:25]C(=O)C2C=CC=CC=2)[O:12][C@@H:11]1[N:34]1[C:41]([CH3:42])=[CH:40][C:38](=[O:39])[NH:37][C:35]1=[O:36])(=O)C1C=CC=CC=1.CC(O)C>N>[C@H:11]1([N:34]2[C:41]([CH3:42])=[CH:40][C:38](=[O:39])[NH:37][C:35]2=[O:36])[O:12][C@@H:13]([CH2:24][OH:25])[C@H:14]([OH:15])[C@@H:10]1[OH:9]

参加物

4

反応物 2

HCID 3776IsopropanolHCID 120432031-(2',3',5'-Tri-O-benzoyl-beta-L-ribofuranosyl)-6-methyluracil

生成物 1

HCID 543042731-beta-L-Ribofuranosyl-6-methyluracil

試薬・触媒・溶媒 1

HCID 222Ammonia溶媒

実験手順

A solution of 40 (4.50 g, 7.86 mmol) was dissolved in sat. methanolic ammonia (60 mL). The reaction mixture was heated at 100° C. for 17 h in a steel bomb. The reaction vessel was cooled to room temperature and concentrated to yield an oil. The reside was further purified by silica gel flash column chromatography using dichloromethane and methanol (9:1) as the eluent. Pure fractions were collected and evaporated to give a white solid. This was further recyrstallized from 2-propanol to afford 1.98 g (94%) of pure 41: mp 175-177° C.; 1H NMR (Me2SO-d6) δ2.24 (s, 3H, CH3), 3.42-3.57 (m, 2H, C5′H), 3.68 (m, 1H, C4′H), 4.0 (m, 1H, C3′H), 4.53 (m, 1H, C2′H), 4.68, 4.94, 5.22 (m, 3H, 3 OH, D2O exchangeable), 5.43 (d, 1H, C1′H, J1′,2′=3.85 Hz), 5.56 (s, 1H, C5H) and 11.25 (s, 1H, NH). Anal. Calc. for C10H14N2O6 (258.23): C, 46.51; H, 5.46; N, 10.85. Found: C, 46.66; H, 5.26; N, 10.66.

後処理

  1. concentrationconcentrated
  2. customto yield an oil
  3. customThe reside was further purified by silica gel flash column chromatography
  4. customPure fractions were collected
  5. customevaporated
  6. customto give a white solid
  7. customto afford 1.98 g (94%) of pure 41

出典と根拠

ORDレコード
ord-3a080408828d406ba1ab4259de6f1432
出典データセット
uspto-grants-2003_11
特許番号
US06642206B2

反応ノート

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