Acetic Acid → HCID 10995419, compound

HRID 727466Notes

Reaction equation

HRID 727466 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]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 22881709HCID 22881709, compound

Product 1

HCID 10995419HCID 10995419, compoundYield 66.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

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 (1L), 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

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. washwashed with 10% brine (500 ml
  3. dry with material2×300 ml), dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude was purified by chromatography on silica (EtOAc-hexane, 3:1)

Sources & evidence

ORD record
ord-507ed52f9243480f8a15334eb68a7f69
Source dataset
uspto-grants-1998_01
Patent number
US05712378

Reaction notes

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