Triethylamine → 4'-C-triethylsilylethynyl-3',5'-di-O-benzyluridine

HRID 2186318Notes

Reaction equation

HRID 2186318 reaction equation
[CH2:1]([Si:3]([C:8]#[C:9][C@:10]1([CH2:35][O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[O:14][C@@H:13]([N:15]2[CH:22]=[CH:21][C:19](=[O:20])[NH:18][C:16]2=[O:17])[C@H:12]([O:23]C(=O)C)[C@@H:11]1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].C(N(CC)CC)C>CO>[CH2:1]([Si:3]([C:8]#[C:9][C@:10]1([CH2:35][O:36][CH2:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[O:14][C@@H:13]([N:15]2[CH:22]=[CH:21][C:19](=[O:20])[NH:18][C:16]2=[O:17])[C@H:12]([OH:23])[C@@H:11]1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 10651295HCID 10651295, compound

Product 1

HCID 107455044'-C-triethylsilylethynyl-3',5'-di-O-benzyluridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 7 (2.00 g, 3.3 mmol) was dissolved in methanol (90.0 ml), and triethylamine (10.0 ml) was added to the solution, followed by stirring for 48 hours at room temperature. The reaction mixture was concentrated through distillation under reduced pressure, and the residue was purified by means of silica gel column chromatography (silica gel 200 ml, eluent; n-hexane:ethyl acetate=1:1), to thereby yield a white powdery compound (Compound 8; 1.72 g, 3.06 mmol, 92.4%).

Workup

  1. concentrationThe reaction mixture was concentrated through distillation under reduced pressure
  2. customthe residue was purified by means of silica gel column chromatography (silica gel 200 ml, eluent; n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-6b58d2a85cfe49cb9efcb16e19976245
Source dataset
uspto-grants-2002_06
Patent number
US06403568B1

Reaction notes

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