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

HRID 478771

반응식

HRID 478771 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 222Ammonia용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3a080408828d406ba1ab4259de6f1432
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06642206B2

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