Dimethylamine tetrahydrofuran → HCID 53253860, compound

HRID 1665825Notes

Reaction equation

HRID 1665825 reaction equation
C([N:9]1[C:56](=[O:57])[CH:55]=[CH:54][N:11]([C@@H:12]2[O:53][C@H:27]([CH2:28][O:29][C:30]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)([C:39]3[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=3)[C:31]3[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=3)[C@@H:25]([OH:26])[C@H:13]2[O:14][CH2:15][CH2:16][C:17]([O:19]CC(F)(F)F)=O)[C:10]1=[O:58])(=O)C1C=CC=CC=1.[CH3:59][NH:60][CH3:61].O1CCCC1>>[CH3:38][O:37][C:34]1[CH:33]=[CH:32][C:31]([C:30]([O:29][CH2:28][C@H:27]2[O:53][C@@H:12]([N:11]3[CH:54]=[CH:55][C:56](=[O:57])[NH:9][C:10]3=[O:58])[C@H:13]([O:14][CH2:15][CH2:16][C:17](=[O:19])[N:60]([CH3:61])[CH3:59])[C@@H:25]2[OH:26])([C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[C:39]2[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=2)=[CH:36][CH:35]=1

Participants

3

Reactant 2

HCID 22320367Dimethylamine tetrahydrofuranHCID 86638307HCID 86638307, compound

Product 1

HCID 53253860HCID 53253860, compound

Procedure

To N3-benzoyl-5′-O-(4,4′-dimethoxytrityl)-2′-O-[2-(2,2,2-trifluoroethoxy)carbonylethyl]uridine (120 mg, 0.15 mmol) synthesized in Example 15 was added 2 M dimethylamine/tetrahydrofuran (4 mL), followed by stirring at room temperature for 15 hours. Then, the reaction was carried out at 40° C. for 2 hours. The solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography eluting with chloroform to give the title compound as a white foam-like material (80 mg, 83%).

Workup

  1. waitThen, the reaction was carried out at 40° C. for 2 hours
  2. customThe solvent was evaporated under reduced pressure
  3. washeluting with chloroform

Sources & evidence

ORD record
ord-c02aa80bef474b7f8c84e014015ca5a8
Source dataset
uspto-grants-2011_10
Patent number
US08039611B2

Reaction notes

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