Trifluoromethanesulfonic anhydride → HCID 136331515, compound

HRID 2408265Notes

Reaction equation

HRID 2408265 reaction equation
[C:1]([O:9][CH2:10][C@H:11]1[O:15][C@@H:14]([N:16]2[C:31]3[N:30]=[C:23]([NH:24][C:25](=[O:29])[CH:26]([CH3:28])[CH3:27])[NH:22][C:20](=[O:21])[C:19]=3[N:18]=[CH:17]2)[CH2:13][C@@H:12]1[OH:32])(=[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.N1C=CC=CC=1>[C:25]([NH:24][C:23]1[NH:22][C:20](=[O:21])[C:19]2[N:18]=[CH:17][N:16]([C@@H:14]3[O:15][C@H:11]([CH2:10][O:9][C:1](=[O:8])[C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[C@H:12]([OH:32])[CH2:13]3)[C:31]=2[N:30]=1)(=[O:29])[CH:26]([CH3:28])[CH3:27]

Participants

5

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 135937358HCID 135937358, compound

Product 1

HCID 136331515HCID 136331515, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 51 (5 g, 11.33 mmol) in anhydrous dichloromethane (200 mL) and anhydrous pyridine (30 mL) was added dropwise trifluoromethanesulfonic anhydride (5.8 mL, 33.99 mmol) at 0° C. After removal of the cooling bath, the reaction was stirred at room temperature for 30 min until the reaction mixture cleared up. Then water (20 mL) was added and the reaction was further stirred for 3 h at room temperature. The organic layer was separated and evaporated. The residual oil was then purified by column chromatography on silica gel eluting with CH2Cl2-MeOH (95:5) yielding the title compound 52 (0.5 g, 10%), together with N2-isobutyryl-9-(3-O-benzoyl-2-deoxy-β-D-threo-pentofuranosyl)-guanine (53) (1.93 g, 39%) and N2-isobutyryl-9-(5-O-benzoyl-2,3-dideoxy-β-D-threo-pentofuranosyl)-(N3→3′)-cycloguanine (54) (0.89 g, 18%).

Workup

  1. customAfter removal of the cooling bath
  2. additionThen water (20 mL) was added
  3. stirringthe reaction was further stirred for 3 h at room temperature
  4. customThe organic layer was separated
  5. customevaporated
  6. customThe residual oil was then purified by column chromatography on silica gel eluting with CH2Cl2-MeOH (95:5)

Sources & evidence

ORD record
ord-7d946b34a08f42cbbaa9a908ad175bb6
Source dataset
uspto-grants-2014_08
Patent number
US08815829B2

Reaction notes

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