Dimethylformamide → 3',5'-o-Bis-tert-butyldimethylsilyl-2'-deoxycytidine

HRID 871791Notes

Reaction equation

HRID 871791 reaction equation
[C@@H:1]1([N:9]2[CH:16]=[CH:15][C:13]([NH2:14])=[N:12][C:10]2=[O:11])[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1.[CH3:17][C:18]([Si:21](Cl)([CH3:23])[CH3:22])([CH3:20])[CH3:19].CN(C=O)C>CO>[Si:21]([C@@:3]1([OH:4])[C@@H:5]([CH2:6][O:7][Si:21]([C:18]([CH3:20])([CH3:19])[CH3:17])([CH3:23])[CH3:22])[O:8][C@@H:1]([N:9]2[CH:16]=[CH:15][C:13]([NH2:14])=[N:12][C:10]2=[O:11])[CH2:2]1)([C:18]([CH3:20])([CH3:19])[CH3:17])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 13711DeoxycytidineHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 1317287263',5'-o-Bis-tert-butyldimethylsilyl-2'-deoxycytidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2′-deoxycytidine dC (2.85 g, 12.54 mmol), imidiazole (6.49 g, 95.31 mmol), and TBSCl (7.18 g, 47.65 mmol) were added to anhydrous DMF (27 mL) and stirred at room temperature overnight under a N2 atmosphere. Methanol (20 mL) was added, and the mixture was stirred for 30 minutes and then concentrated in vacuo. Ethyl acetate (60 mL) and water (60 mL) were then added. The organic layer was separated and washed twice with water (20 mL), and the combined aqueous layer was extracted with ethyl acetate (20 mL). The combined organic layer was dried with Na2SO4, concentrated in vacuo, and purified by silica gel chromatography to give 3′,5′-O-bis-tert-butyldimethylsilyl-2′-deoxycytidine dC.01 (4.79 g, 84%) as a white foam.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. concentrationconcentrated in vacuo
  3. additionEthyl acetate (60 mL) and water (60 mL) were then added
  4. customThe organic layer was separated
  5. washwashed twice with water (20 mL)
  6. extractionthe combined aqueous layer was extracted with ethyl acetate (20 mL)
  7. dry with materialThe combined organic layer was dried with Na2SO4
  8. concentrationconcentrated in vacuo
  9. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-e3e63375f4f843799ad7a8050e4cacfe
Source dataset
uspto-grants-2015_03
Patent number
US08969535B2

Reaction notes

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