Acetic Acid → HCID 10995419, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:42]=[CH:41][C:6]([C:7]([O:22][C@@H:23]2[C@@H:27]([CH:28](C=O)[OH:29])[O:26][C@@H:25]([N:32]3[CH:40]=[C:38]([CH3:39])[C:36](=[O:37])[NH:35][C:33]3=[O:34])[CH2:24]2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:13]=[CH:12][C:11](OC)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[CH2:43]=[O:44].[OH-].[Na+].[C:47]([OH:50])(=O)C>O1CCOCC1.O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:42]=[CH:41][C:6]([C:7]([O:22][C@@H:23]2[C:27]([CH2:28][OH:29])([CH2:47][OH:50])[O:26][C@@H:25]([N:32]3[CH:40]=[C:38]([CH3:39])[C:36](=[O:37])[NH:35][C:33]3=[O:34])[CH2:24]2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:13]=[CH:12][C:11]([O:44][CH3:43])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1Participants
8
Procedure
To a stirred solution of 3′-O-(4,4′dimethoxytrityl)-5′-formylthymidine (16.3 g, 30.07 mmol) in dioxane (120 ml) at 0° C. was added dropwise, in turn, 36% formaldehyde (24 ml) and 2N NaOH (60 ml). The resulting solution was stirred at room temperature for 6 h. The reaction mixture was cooled to 0° C. and 10% acetic acid in water added dropwise until pH reached 7.5. The mixture was diluted with ethyl acetate (1 L), washed with 10% brine (500 ml, then 2×300 ml), dried (Na2SO4), and concentrated. The crude was purified by chromatography on silica (EtOAc-hexane, 3:1) to give 11.45 g (66.3%) of 3′-O-(4,4′-dimethoxytrityl)-4′-C-hydroxymethylthymidine as a colorless powder.
Workup
- temperatureThe reaction mixture was cooled to 0° C.
- washwashed with 10% brine (500 ml
- dry with material2×300 ml), dried (Na2SO4)
- concentrationconcentrated
- customThe crude was purified by chromatography on silica (EtOAc-hexane, 3:1)
Sources & evidence
- ORD record
- ord-b8343b2c78734ad0919aa7ed3441dec0
- Source dataset
- uspto-grants-2004_06
- Patent number
- US06743902B1
Reaction notes
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