Chlorotrimethylsilane → HCID 22874774, compound

HRID 341940Notes

Reaction equation

HRID 341940 reaction equation
[CH2:1]([O:4][C@@H:5]1[C@H:9]([OH:10])[C@@H:8]([CH2:11][OH:12])[O:7][C@H:6]1[N:13]1[CH:20]=[CH:19][C:17]([NH2:18])=[N:16][C:14]1=[O:15])[CH2:2][CH3:3].C[Si](Cl)(C)C.[C:26](Cl)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[NH4+].[OH-]>O.N1C=CC=CC=1>[C:26]([NH:18][C:17]1[CH:19]=[CH:20][N:13]([C@@H:6]2[O:7][C@H:8]([CH2:11][OH:12])[C@@H:9]([OH:10])[C@H:5]2[O:4][CH2:1][CH2:2][CH3:3])[C:14](=[O:15])[N:16]=1)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 7412Benzoyl chlorideHCID 14923Ammonium HydroxideHCID 228747462'-O-Propylcytidine2×

Product 1

HCID 22874774HCID 22874774, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To the 2'-O-propylcytidine reaction mixture of Example 82 in an ice bath was added pyridine (60 ml) and trimethylsilyl chloride (60 ml). The reaction was stirred for 30 mins followed by the addition of benzoyl chloride (55 ml). The resulting reaction mixture was stirred for 2.5 hrs and then cooled in an ice bath. H2O (100 ml) and conc. NH4OH (100 ml) were added. After stirring for 30 mins, the reaction mixture was evaporated and the residue partition between H2O and CH2Cl2. The organic phase was washed once with dil Na2CO3, once with dil HCl, dried over MgSO4 and evaporated. The resulting residue was loaded on a silica gel column (150 g) and eluted with first CH2Cl2 then 5 to 10% MeOH in CH2Cl2 as the elution solvent. The product containing fractions were evaporated to a foam. The foam was crystallized from EtOAc/Hexanes to give the product (6.5 g total) in several crystal batches.

Workup

  1. customThe resulting reaction mixture
  2. stirringwas stirred for 2.5 hrs
  3. temperaturecooled in an ice bath
  4. stirringAfter stirring for 30 mins
  5. customthe reaction mixture was evaporated
  6. customthe residue partition between H2O and CH2Cl2
  7. washThe organic phase was washed once with dil Na2CO3, once with dil HCl
  8. dry with materialdried over MgSO4
  9. customevaporated
  10. washeluted with first CH2Cl2
  11. additionThe product containing fractions
  12. customwere evaporated to a foam
  13. customThe foam was crystallized from EtOAc/Hexanes
  14. customto give the product (6.5 g total) in several crystal batches

Sources & evidence

ORD record
ord-4ab1211361a641b088e8d4c29aac2dcc
Source dataset
uspto-grants-1999_01
Patent number
US05856466

Reaction notes

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