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

HRID 1007608Notes

Reaction equation

HRID 1007608 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-0b40384accf94b67bf2c5b5cd6e9191e
Source dataset
uspto-grants-2004_09
Patent number
US06794499B2

Reaction notes

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