Trityl chloride → HCID 11431328, compound

HRID 1818665Notes

Reaction equation

HRID 1818665 reaction equation
[NH2:1][CH2:2][C@H:3]1[O:7][C@@H:6]([N:8]2[CH:15]=[CH:14][C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5][C@@H:4]1[OH:16].[C:17](Cl)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>N1C=CC=CC=1>[C:17]([NH:1][CH2:2][C@H:3]1[O:7][C@@H:6]([N:8]2[CH:15]=[CH:14][C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5][C@@H:4]1[OH:16])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 451827Uridine, 5'-amino-2',5'-dideoxy-

Product 1

HCID 11431328HCID 11431328, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

5′-Amino-2′,5′-dideoxyuridine (0.200 g, 0.88 mmol) was taken in dry pyridine (5 mL) and the mixture was sonicated for a few minutes. Trityl chloride (0.278 g, 1.00 mmol) was added and the reaction mixture was stirred at 50° C. overnight. The reaction was then quenched with water (20 mL). The crude mixture was extracted with DCM (3×10 mL). The organic layers were combined, washed with water (10 mL), dried over MgSO4 and concentrated on the rotary evaporator. The resultant brown oil was further purified by silica gel column chromatography (Isolute Si column) using a gradient elution of 0→10% CH3OH in CHCl3. The fractions with Rf=0.28 (10% CH3OH/CHCl3) were pooled and evaporated to dryness to yield the title compound as a white solid (0.202 g, 49%).

Workup

  1. customthe mixture was sonicated for a few minutes
  2. customThe reaction was then quenched with water (20 mL)
  3. extractionThe crude mixture was extracted with DCM (3×10 mL)
  4. washwashed with water (10 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated on the rotary evaporator
  7. customThe resultant brown oil was further purified by silica gel column chromatography (Isolute Si column)
  8. washa gradient elution of 0→10% CH3OH in CHCl3
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-64f198f13ab844388c384c16a7ebc4f8
Source dataset
uspto-grants-2009_10
Patent number
US07601702B2

Reaction notes

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