1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → HCID 15546053, compound

HRID 434275Notes

Reaction equation

HRID 434275 reaction equation
[OH:1][C@H:2]1[C@H:6]2[O:7][CH2:8][C@:3]1([CH2:17][OH:18])[O:4][C@H:5]2[N:9]1[CH:16]=[CH:15][C:13](=[O:14])[NH:12][C:10]1=[O:11].[CH3:19][O:20][C:21]1[CH:42]=[CH:41][C:24]([C:25](Cl)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)=[CH:23][CH:22]=1>N1C=CC=CC=1>[CH3:33][O:32][C:29]1[CH:28]=[CH:27][C:26]([C:25]([O:18][CH2:17][C@@:3]23[C@@H:2]([OH:1])[C@@H:6]([O:7][CH2:8]2)[C@H:5]([N:9]2[CH:16]=[CH:15][C:13](=[O:14])[NH:12][C:10]2=[O:11])[O:4]3)([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:24]2[CH:41]=[CH:42][C:21]([O:20][CH3:19])=[CH:22][CH:23]=2)=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 15546052HCID 15546052, compound

Product 1

HCID 15546053HCID 15546053, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of compound 44 (0.08 g, 0.31 mmol) in anhydrous pyridine (0.5 cm3) was added 4,4′-dimethoxytrityl chloride (0.203 g, 0.6 mmol) at 0° C. and the mixture was stirred at room temperature for 2 h. The reaction was quenched with ice-cold water (10 cm3) and extracted with dichloromethane (3×4 cm3). The combined organic phase was washed with saturated aqueous solutions of sodium hydrogencarbonate (3×3 cm3) and brine (2×3 cm3) and was dried (Na2SO4). The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography using dichloromethane/methanol (98:2, v/v) as eluent to give nucleoside 45 as a white solid material (0.12 g, 69%). δH (CDCl3) 9.25 (1H, br s, NH), 7.93 (1H, d, J 7.2, 6-H), 7.50-7.15 (9H, m, DMT), 6.88-6.78 (4H, m, DMT), 5.63 (1H, s, 1′-H), 5.59 (1H, d, J 8.0, 5-H), 4.48 (1H, s, 2′-H), 4.26 (1H, s, 3′-H), 3.88 (1H, d, J 8.1, 1″-Ha), 3.85-3.55 (7H, m, 1″-Hb, OCH3), 3.58-3.40 (2H, m, 5′-Ha, 5′-Hb). δC (CDCl3) 164.10 (C-4), 158.60 (DMT), 150.45 (C-2), 147.53 (DMT), 144.51 (C-6), 139.72, 135.49, 135.37, 130.20, 129.28, 128.09, 127.85, 127.07 (DMT), 113.39, 113.17 (DMT), 101.79 (C-5), 88.20, 87.10, 86.87 (C-1′, C-4′, DMT), 79.25, 71.79, 69.70, 58.13 (C-2′, C-3′, C-5′, C-1″), 55.33 (OCH3). FAB-MS m/z 559 [M+H]+.

Workup

  1. customThe reaction was quenched with ice-cold water (10 cm3)
  2. extractionextracted with dichloromethane (3×4 cm3)
  3. washThe combined organic phase was washed with saturated aqueous solutions of sodium hydrogencarbonate (3×3 cm3) and brine (2×3 cm3)
  4. dry with materialwas dried (Na2SO4)
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c6fbb210492842e2b9891edd40d0dd70
Source dataset
uspto-grants-2003_12
Patent number
US06670461B1

Reaction notes

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