1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → HCID 13009020, compound

HRID 1663544Notes

Reaction equation

HRID 1663544 reaction equation
[OH:1][C@H:2]1[C@H:6]2[O:7][CH2:8][C@:3]1([CH2:27][OH:28])[O:4][C@H:5]2[N:9]1[CH:17]=[N:16][C:15]2[C:10]1=[N:11][CH:12]=[N:13][C:14]=2[NH:18][C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[CH3:29][O:30][C:31]1[CH:52]=[CH:51][C:34]([C:35](Cl)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:36]2[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=2)=[CH:33][CH:32]=1.C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[OH:1][C@H:2]1[C@H:6]2[O:7][CH2:8][C@:3]1([CH2:27][O:28][C:35]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=1)[C:34]1[CH:33]=[CH:32][C:31]([O:30][CH3:29])=[CH:52][CH:51]=1)[O:4][C@H:5]2[N:9]1[CH:17]=[N:16][C:15]2[C:10]1=[N:11][CH:12]=[N:13][C:14]=2[NH:18][C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[OH:1][C@H:2]1[C@H:6]2[O:7][CH2:8][C@:3]1([CH2:27][OH:28])[O:4][C@H:5]2[N:9]1[CH:17]=[N:16][C:15]2[C:10]1=[N:11][CH:12]=[N:13][C:14]=2[NH2:18]

Participants

6

Reactant 3

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 516892Sodium BicarbonateHCID 11069003HCID 11069003, compound

Product 2

HCID 13009020HCID 13009020, compoundHCID 44436074HCID 44436074, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of compound 61B (0.50 g) in anhydrous pyridine (20 cm3) was added 4,4′-dimethoxytrityl chloride (0.71 g, 2.09 mmol) and 4-N,N-dimethylaminopyridine (DMAP) (0.1 g). After stirring for 2 h at room temperature and for 1 h at 50° C., the reaction mixture was cooled to 0° C. and a saturated aqueous solution of sodium hydrogencarbonate (100 cm3) was added. After extraction using dichloromethane (3×50 cm3), the combined organic phase was dried (Na2SO4) and evaporated under reduced pressure. The residue was purified by silica gel column chromatography eluting with dichloromethane/methanol/pyridine (98.0:1.5:0.5) to give nucleoside 61C as a white solid material (0.36 g, ˜50% from 61A). δH (C5D5N) 12.52 (NHCO), 9.10 (2H, d, J 7.7, Bz), 8.88 (1H, s, 8-H), 8.50-7.11 (17H, m, DMT, Bz, 2-H), 6.65 (1H, s, H-1′), 5.25 (2H, s, H-2′, H-3′), 4.71 (1H, d, J 7.8, 1″-Ha), 4.56 (1H, d, J 7.8, 1″-Hb), 4.20 (1H, d, J 10.8, 5′-Ha), 4.07 (1H, d, J 10.8, 5′-Hb), 3.82, 3.81 (2×3H, 2×s, 2×OCH3). δC (C5D5N) 167.56 (NHCO), 159.24 (C-6), 152.50, 152.08, 151.81, 145.84, 141.45, 136.52, 136.28, 132.55, 130.76, 130.70, 129.32, 128.85, 128.76, 128.46, 127.38, 126.33 (DMT, Bz, C-2, C-4, C-8), 113.84 (C-5), 88.64, 87.20, 86.85, 80.52, 73.13, 72.16, 60.86 (C-1′, C-4′, DMT, C-2′, C-3′, C-1″, C-5′), 55.24 (OCH3). FAB-MS m/z 686 [M+H]+. Found: C, 68.3; H, 5.0; N, 9.7; C39H35N5O7 requires C, 68.3; H, 5.1; N, 10.2%).

Workup

  1. temperaturethe reaction mixture was cooled to 0° C.
  2. extractionAfter extraction
  3. dry with materialthe combined organic phase was dried (Na2SO4)
  4. customevaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography
  6. washeluting with dichloromethane/methanol/pyridine (98.0:1.5:0.5)

Sources & evidence

ORD record
ord-f9b7e3e09b744a52b499fa051a12ee6f
Source dataset
uspto-grants-2011_10
Patent number
US08034909B2

Reaction notes

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