Trityl chloride → 3'-(Trityl)amino-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxyuridine

HRID 342917Notes

Reaction equation

HRID 342917 reaction equation
[N:1]([C@@H:4]1[C@@H:8]([CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[O:7][C@@H:6]([N:18]2[CH:25]=[CH:24][C:22](=[O:23])[NH:21][C:19]2=[O:20])[CH2:5]1)=[N+]=[N-].C(N(CC)CC)C.[C:33](Cl)([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(Cl)Cl.N1C=CC=CC=1>[C:33]([NH:1][C@@H:4]1[C@@H:8]([CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[O:7][C@@H:6]([N:18]2[CH:25]=[CH:24][C:22](=[O:23])[NH:21][C:19]2=[O:20])[CH2:5]1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1)[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 107851963'-Azido-5'-O-tert-butyldimethylsilyl-2',3'-dideoxyuridine

Product 1

HCID 107458583'-(Trityl)amino-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxyuridineYield 85%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 6344DichloromethaneSolvent

Procedure

3'-(Trityl)amino-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxyuridine, 2du. Crude 1du (33.2 g, 90.3 mmol) was dissolved in 2:1 EtOH/CH2Cl2 (300 mL) and reduced via hydrogenation (60 psi H2) in the presence of 10% Pd/C (3.0 g) for 18 h. Subsequent removal of the catalyst via filtration and evaporation of solvent in vacuo, afforded quantitative yield (30.4 g, 89.8 mmol) of the corresponding 3'-amine which was taken on directly to the next reaction. The 5'-O-(tert-butyldimethylsilyl)-3'-amino-2',3'-dideoxyuridine (30.4 g, 89.8 mmol) was azeotroped from pyridine (2×300 mL), and dissolved in a mixture of CH2Cl2 (600 mL) and anhydrous pyridine (70 mL). To this solution was added triethylamine (25.0 mL, 179.6 mmol) and trityl chloride (35.0 g, 125.7 mmol), and the reaction mixture was stirred for 2 h at ambient temperature. Solvents were removed in vacuo, and the crude product was purified on silica (1-5% MeOH/CH2Cl2) to afford 85% yield (44.3 g, 75.9 mmol) of 3'-(Trityl)amino-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxyuridine, 2du.

Workup

  1. customdirectly to the next reaction
  2. customSolvents were removed in vacuo
  3. customthe crude product was purified on silica (1-5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-57ba66be2ddb469bb5c49f17a67380a4
Source dataset
uspto-grants-1999_01
Patent number
US05859233

Reaction notes

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