Trifluoroacetic acid → 1-(2-{2-[(Ethoxycarbonyl)methoxy]-phenyl}-2-oxo-ethyl)-3-methyl-7-(3-methyl-2-buten-1-yl)-8-(3-amino-piperidin-1-yl)-xanthine

HRID 515529Notes

Reaction equation

HRID 515529 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14](=[O:47])[CH2:15][N:16]1[C:25](=[O:26])[C:24]2[N:23]([CH2:27][CH:28]=[C:29]([CH3:31])[CH3:30])[C:22]([N:32]3[CH2:37][CH2:36][CH2:35][CH:34]([NH:38]C(OC(C)(C)C)=O)[CH2:33]3)=[N:21][C:20]=2[N:19]([CH3:46])[C:17]1=[O:18])=[O:5])[CH3:2].FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([O:3][C:4]([CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14](=[O:47])[CH2:15][N:16]1[C:25](=[O:26])[C:24]2[N:23]([CH2:27][CH:28]=[C:29]([CH3:30])[CH3:31])[C:22]([N:32]3[CH2:37][CH2:36][CH2:35][CH:34]([NH2:38])[CH2:33]3)=[N:21][C:20]=2[N:19]([CH3:46])[C:17]1=[O:18])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 667537501-(2-{2-[(Ethoxycarbonyl)methoxy]-phenyl}-2-oxo-ethyl)-3-methyl-7-(3-methyl-2-buten-1-yl)-8-[3-(tert.-butyloxycarbonylamino)-piperidin-1-yl]-xanthine

Product 1

HCID 100763101-(2-{2-[(Ethoxycarbonyl)methoxy]-phenyl}-2-oxo-ethyl)-3-methyl-7-(3-methyl-2-buten-1-yl)-8-(3-amino-piperidin-1-yl)-xanthine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 209 mg of 1-(2-{2-[(ethoxycarbonyl)methoxy]-phenyl}-2-oxo-ethyl)-3-methyl-7-(3-methyl-2-buten-1-yl)-8-[3-(tert.-butyloxycarbonylamino)-piperidin-1-yl]-xanthine in 4 ml methylene chloride is combined with 1 ml of trifluoroacetic acid and stirred for half an hour at ambient temperature. For working up the reaction mixture is diluted with methylene chloride and washed with saturated potassium carbonate solution. The organic phase is dried, evaporated down and chromatographed through a silica gel column with methylene chloride/methanol (1:0 to 4:1) as eluant.

Workup

  1. washwashed with saturated potassium carbonate solution
  2. customThe organic phase is dried
  3. customevaporated down
  4. customchromatographed through a silica gel column with methylene chloride/methanol (1:0 to 4:1) as eluant

Sources & evidence

ORD record
ord-15816035887a42edac758249ae6603c3
Source dataset
uspto-grants-2015_08
Patent number
US09108964B2

Reaction notes

Loading…