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Methanol → 5'-O-(t-Butyldimethylsilyl)-2',3'-dideoxy-3'-diazo-2'-oxo-uridine

HRID 234977
Notes
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Reaction equation

HRID 234977 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]1[O:14][C@@H:13]([N:15]2[CH:22]=[CH:21][C:19](=[O:20])[NH:18][C:16]2=[O:17])[C:12](=[O:23])[C:11]1=CN(C)C)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].FC(F)(F)S([N:33]=[N+:34]=[N-])(=O)=O.CO>C(Cl)Cl>[Si:1]([O:8][CH2:9][C@H:10]1[O:14][C@@H:13]([N:15]2[CH:22]=[CH:21][C:19](=[O:20])[NH:18][C:16]2=[O:17])[C:12](=[O:23])[C:11]1=[N+:33]=[N-:34])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 887MethanolHCID 10986786Methanesulfonyl azide, trifluoro-HCID 677174835'-O-(t-Butyldimethylsilyl)-2',3'-dideoxy-3'-(N,N-dimethylaminomethylene)-2'-oxo-uridine

Product 1

HCID 867486945'-O-(t-Butyldimethylsilyl)-2',3'-dideoxy-3'-diazo-2'-oxo-uridineYield 77%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Conditions

Temperature
60 °C

Procedure

5'-O-(t-Butyldimethylsilyl)-2',3'-dideoxy-3'-(N,N-dimethylamino-methylene)-2'-oxo-uridine (1.78 g, 4.5 mmol), from Step 6, was added to the trifluoromethanesulfonyl azide solution and the reaction mixture was heated at 60° C. for 2.5 h under a nitrogen atmosphere. The solvents were evaporated in vacuo to a syrup (2.8 g) which was dissolved in 10 mL of methylene chloride and purified by flash chromatography (5 psi) on a silica gel column (2×35 cm) eluted with 200 mL of methylene chloride, 200 mL of 1% methanol in methylene chloride, 200 mL of 2% methanol in methylene chloride and 3% methanol in methylene chloride to give 1.27 g (77% yield) of the title compound. MS DCI: 367 (M+H)+.

Workup

  1. customThe solvents were evaporated in vacuo to a syrup (2.8 g) which
  2. dissolutionwas dissolved in 10 mL of methylene chloride
  3. custompurified by flash chromatography (5 psi) on a silica gel column (2×35 cm)
  4. washeluted with 200 mL of methylene chloride, 200 mL of 1% methanol in methylene chloride, 200 mL of 2% methanol in methylene chloride

Sources & evidence

ORD record
ord-fe624a0cbf0d4b9abc15969289b3308b
Source dataset
uspto-grants-1997_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05597824

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes