1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → HCID 136395924, compound

HRID 1379762Notes

Reaction equation

HRID 1379762 reaction equation
[N:1]#[N:2].[C:3]([C@@:8]1([N:16]2[C:26]3[N:25]=[C:23]([NH2:24])[NH:22][C:20](=[O:21])[C:19]=3[N:18]=[CH:17]2)[O:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[CH2:9]1)(=[O:7])[CH:4]([CH3:6])[CH3:5].[CH3:27][O:28][C:29]1[CH:50]=[CH:49][C:32]([C:33](Cl)([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=2)=[CH:31][CH:30]=1>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[N:1]#[N:2].[C:3]([C@@:8]1([N:16]2[C:26]3[N:25]=[C:23]([NH2:24])[NH:22][C:20](=[O:21])[C:19]=3[N:18]=[CH:17]2)[O:15][C@H:12]([CH2:13][O:14][C:33]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)([C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=2)[C:32]2[CH:31]=[CH:30][C:29]([O:28][CH3:27])=[CH:50][CH:49]=2)[C@@H:10]([OH:11])[CH2:9]1)(=[O:7])[CH:4]([CH3:6])[CH3:5]

Participants

5

Reactant 2

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 136395926N2 isobutyryl-2'-deoxyguanosine

Product 1

HCID 136395924HCID 136395924, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent2×

Procedure

The tritylation procedure of Jones45 was modified such that no DMAP was used. To 3.37 g (10.0 mmol) of N2 -isobutyryl-2'-deoxyguanosine (that was first concentrated from dry pyridine) in 50 mL of dry pyridine, was added 4.06 g (12.0 mmol, 1.20 equiv.) of 4,4'-dimethoxytrityl chloride. The reaction was stirred for 15 h, and then concentrated. The residue was partitioned between CH2Cl2 and 0.5% aq. NaHCO3, shaken, and separated. The organic layer was washed with 0.5% aq. NaHCO3 and dried. The crude product was purified by flash chromatography.

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between CH2Cl2 and 0.5% aq. NaHCO3
  3. stirringshaken
  4. customseparated
  5. washThe organic layer was washed with 0.5% aq. NaHCO3
  6. customdried
  7. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-17e30a977b3048eea8c1eb5609395ca2
Source dataset
uspto-grants-1997_09
Patent number
US05672697

Reaction notes

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