Trifluoroacetic anhydride → (R)-1-(5-acetoxyhexyl)-7-benzyl-3-methyl 8-(N-(trifluoroacetoxy)aminomethyl)xanthine

HRID 1296407Notes

Reaction equation

HRID 1296407 reaction equation
[C:1]([O:4][C@H:5]([CH3:31])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]([CH2:28][NH2:29])=[N:15][C:14]=2[N:13]([CH3:30])[C:11]1=[O:12])(=[O:3])[CH3:2].[F:32][C:33]([F:44])([F:43])[C:34]([O:36]C(=O)C(F)(F)F)=[O:35]>C(Cl)(Cl)Cl>[C:1]([O:4][C@H:5]([CH3:31])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]([CH2:28][NH:29][O:36][C:34](=[O:35])[C:33]([F:44])([F:43])[F:32])=[N:15][C:14]=2[N:13]([CH3:30])[C:11]1=[O:12])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 54253673(R)-1-(5-acetoxyhexyl)-8-aminomethyl-7-benzyl-3-methylxanthine

Product 1

HCID 86585572(R)-1-(5-acetoxyhexyl)-7-benzyl-3-methyl 8-(N-(trifluoroacetoxy)aminomethyl)xanthineYield 95%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A stirring solution of (R)-1-(5-acetoxyhexyl)-8-aminomethyl-7-benzyl-3-methylxanthine in chloroform (30 ml) was treated with trifluoroacetic anhydride (1.0 g, 4.76 mmol) and stirred for 3 hours. Concentration under reduced pressure gave a residue which was purified by flash chromatography on silica gel eluting with ethyl acetate to provide (R)-1-(5-acetoxyhexyl)-7-benzyl-3-methyl 8-(N-(trifluoroacetoxy)aminomethyl)xanthine (1.0 g, 95% yield) as a white powder.

Workup

  1. concentrationConcentration under reduced pressure
  2. customgave a residue which
  3. customwas purified by flash chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-fe907f1574674efabe029595d5cb4986
Source dataset
uspto-grants-2007_07
Patent number
US07247630B2

Reaction notes

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