Trifluoromethanesulfonic anhydride → HCID 13964206, compound

HRID 2258065Notes

Reaction equation

HRID 2258065 reaction equation
[C:1]([NH:9][C:10]1[C:11]2[N:12]=[CH:13][N:14]([C:31]=2[N:32]=[CH:33][N:34]=1)[C@@H:15]1[O:30][C@H:19]([CH2:20][O:21][C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C@@H:17]([OH:18])[CH2:16]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O>ClCCl>[C:1]([NH:9][C:10]1[N:34]=[CH:33][N:32]=[C:31]2[C:11]=1[N:12]=[CH:13][N:14]2[C@@H:15]1[O:30][C@H:19]([CH2:20][O:21][C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C@H:17]([OH:18])[CH2:16]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 11224941HCID 11224941, compound

Product 1

HCID 13964206HCID 13964206, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 920 mg (2 mmol) of N6,5'-O-dibenzoyl-2'-deoxyadenosine (was prepared by the method described by Nishino et al., Nucleosides & Nucleotides 1986, 5, 159) in 30 ml of abs. dichloromethane (contains 2 ml of pyridine) is cooled to -30° C., and 5 ml of a solution of trifluoromethanesulfonic anhydride in dichloromethane (10% by vol.) are slowly added dropwise. After removal of the cooling bath, the solution is left to warm and 1 ml of water is added. After 3 h, a further 5 ml of water are added and the organic phase is washed. After removal of the solvent, the remaining residue is dissolved in 50 ml of methanol, and 100 mg of sodium bicarbonate are added. The mixture is stirred for a further 2 h at RT, neutralized with 10% strength acetic acid, the solvent is removed by distillation, and purification is carried out by flash chromatography on silica gel (chloroform:methanol 97:3). Yield 710 mg (1.48 mmol) 75%. Rf chloroform:methanol 97:3=0.49. MS=459.

Workup

  1. customwas prepared by the method
  2. customAfter removal of the cooling bath
  3. waitthe solution is left
  4. temperatureto warm
  5. addition1 ml of water is added
  6. additiona further 5 ml of water are added
  7. washthe organic phase is washed
  8. customAfter removal of the solvent
  9. dissolutionthe remaining residue is dissolved in 50 ml of methanol
  10. addition100 mg of sodium bicarbonate are added
  11. customthe solvent is removed by distillation, and purification

Sources & evidence

ORD record
ord-617734339de14cf5a27e0bfd0e562993
Source dataset
uspto-grants-1997_08
Patent number
US05659025

Reaction notes

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