Trifluoroacetic acid → HCID 10367176, compound

HRID 227221Notes

Reaction equation

HRID 227221 reaction equation
[CH2:1]([O:8][C:9]([CH2:11][N:12]1[C:21](=[O:22])[C:20]2[N:19]([CH2:23][C:24]#[C:25][CH3:26])[C:18]([N:27]3[CH2:32][CH2:31][CH2:30][C@@H:29]([NH:33]C(OC(C)(C)C)=O)[CH2:28]3)=[N:17][C:16]=2[N:15]([CH3:41])[C:13]1=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.[OH-].[Na+]>C(Cl)Cl>[CH2:1]([O:8][C:9]([CH2:11][N:12]1[C:21](=[O:22])[C:20]2[N:19]([CH2:23][C:24]#[C:25][CH3:26])[C:18]([N:27]3[CH2:32][CH2:31][CH2:30][C@@H:29]([NH2:33])[CH2:28]3)=[N:17][C:16]=2[N:15]([CH3:41])[C:13]1=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 11657016HCID 11657016, compound

Product 1

HCID 10367176HCID 10367176, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

213 mg of 1-[(benzyloxycarbonyl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-[(R)-3-(tert.-butyloxycarbonylamino)-piperidin-1-yl]-xanthine in 2 ml methylene chloride are combined with 1 ml of trifluoroacetic acid and the reaction mixture is shaken for 20 minutes at 30° C. For working up it is made alkaline with 15 ml of 1 N sodium hydroxide solution and the organic phase is separated off. The aqueous phase is extracted with methylene chloride and the combined organic phases are evaporated down. The flask residue is purified through a silica gel column with methylene chloride/methanol (100:0 to 70:30) as eluant.

Workup

  1. customthe organic phase is separated off
  2. extractionThe aqueous phase is extracted with methylene chloride
  3. customthe combined organic phases are evaporated down
  4. customThe flask residue is purified through a silica gel column with methylene chloride/methanol (100:0 to 70:30) as eluant

Sources & evidence

ORD record
ord-c56b1f38c5d74fbf89f8811bcbd08d5f
Source dataset
uspto-grants-2009_07
Patent number
US07560450B2

Reaction notes

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