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

HRID 1689652Notes

Reaction equation

HRID 1689652 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
0 °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 stiffing 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. extractionAfter extraction
  2. dry with materialthe combined organic phase was dried (Na2SO4)
  3. customevaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography
  5. washeluting with dichloromethane/methanol/pyridine (98.0:1.5:0.5)

Sources & evidence

ORD record
ord-d0314f10199746c0b6d990cf0acd0b16
Source dataset
uspto-grants-2012_04
Patent number
US08153365B2

Reaction notes

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