Methanol → HCID 44436074, compound

HRID 1663542Notes

Reaction equation

HRID 1663542 reaction equation
C([O:8][C@H:9]1[C@H:13]2[O:14][CH2:15][C@:10]1([CH2:34][O:35]CC1C=CC=CC=1)[O:11][C@H:12]2[N:16]1[CH:24]=[N:23][C:22]2[C:17]1=[N:18][CH:19]=[N:20][C:21]=2[NH:25]C(=O)C1C=CC=CC=1)C1C=CC=CC=1.B(Cl)(Cl)Cl.CO>ClCCl>[OH:8][C@H:9]1[C@H:13]2[O:14][CH2:15][C@:10]1([CH2:34][OH:35])[O:11][C@H:12]2[N:16]1[CH:24]=[N:23][C:22]2[C:17]1=[N:18][CH:19]=[N:20][C:21]=2[NH2:25]

Participants

5

Reactant 3

HCID 887MethanolHCID 25135Boron Trichloride2×HCID 20610790HCID 20610790, compound

Product 1

HCID 44436074HCID 44436074, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of nucleoside 61 (0.80 g, 1.42 mmol) in anhydrous dichloromethane (30 cm3) at −78° C. was dropwise during 30 min added BCl3 (1 M solution in hexane; 11.36 cm3, 11.36 mmol). The mixture was stirred for 4 h at −78° C., additional BCl3 (1M solution in hexane, 16.0 cm3, 16.0 mmol) was added drop-wise, and the mixture was stirred at −78° C. for 3 h. Then the temperature of the reaction mixture was raised slowly to room temperature and stirring was continued for 30 min. Methanol (25.0 cm3) was added at −78° C., and the mixture was stirred at room temperature for 12 h. The mixture was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography using dichloromethane/methanol (92:8, v/v) as eluent to give nucleoside 61A as a white solid material (0.332 g, 84%). δH ((CD3)2SO) 8.22 (1H, s, 8-H), 8.15 (1H, s, 2-H), 7.33 (2H, s, NH2), 5.89 (1H, s, 1′-H), 5.83 (1H, d, J 4.2, 3′-OH), 5.14 (1H, t, J 5.9, 5′-OH), 4.14 (1H, s, 2′-H), 4.25 (1H, d, J 4.2, 3′-H), 3.92 (1H, d, J 7.8, 1″-Ha), 3.81-3.41 (3H, m, 5′-Ha, 1″-Hb). Oc ((CD3)2SO) 155.90 (C-6), 152.64 (C-2), 148.35 (C-4), 137.72 (C-8), 118.94 (C-5), 88.48, 85.17 (C-1′, C-4′), 79.09, 71.34, 69.83, 56.51 (C-2′, C-3′, C-1″, C-5′). FAB-MS m/z 280 [M+H]+.

Workup

  1. stirringthe mixture was stirred at −78° C. for 3 h
  2. temperatureThen the temperature of the reaction mixture was raised slowly to room temperature
  3. stirringstirring
  4. waitwas continued for 30 min
  5. stirringthe mixture was stirred at room temperature for 12 h
  6. customThe mixture was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f1630b6bfad448aea6fe479afb2c875e
Source dataset
uspto-grants-2011_10
Patent number
US08034909B2

Reaction notes

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