Trifluoroacetic acid → HCID 10097226, compound

HRID 1174570Notes

Reaction equation

HRID 1174570 reaction equation
[CH:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[O:43])[CH2:11][N:12]1[C:21](=[O:22])[C:20]2[N:19]([CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])[C:18]([N:28]3[CH2:33][CH2:32][CH2:31][CH:30]([NH:34]C(OC(C)(C)C)=O)[CH2:29]3)=[N:17][C:16]=2[N:15]([CH3:42])[C:13]1=[O:14])=[O:2].FC(F)(F)C(O)=O.[OH-].[Na+]>C(Cl)Cl>[CH:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[O:43])[CH2:11][N:12]1[C:21](=[O:22])[C:20]2[N:19]([CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])[C:18]([N:28]3[CH2:33][CH2:32][CH2:31][CH:30]([NH2:34])[CH2:29]3)=[N:17][C:16]=2[N:15]([CH3:42])[C:13]1=[O:14])=[O:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 17964863HCID 17964863, compound

Product 1

HCID 10097226HCID 10097226, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 180 mg of 1-[2-(2-formylaminophenyl)-2-oxoethyl]-3-methyl-7-(3-methyl-2-buten-1-yl)-8-[3-(tert-butyloxycarbonylamino)piperidin-1-yl]xanthine in 4 mL of 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 made slightly alkaline with 1 N sodium hydroxide solution and the aqueous phase is extracted with methylene chloride. The combined organic phases are evaporated down and purified through a silica gel column. Yield: 130 mg (87% of theory); Rf value: 0.38 (Ready-made reversed phase TLC plate (E. Merck), acetonitrile/water/trifluoroacetic acid (100:100:0.1)); mass spectrum (ESI+): m/z=494 [M+H]+.

Workup

  1. extractionthe aqueous phase is extracted with methylene chloride
  2. customThe combined organic phases are evaporated down
  3. custompurified through a silica gel column

Sources & evidence

ORD record
ord-b3f4e4c7e9074978a2bf270f92321ef3
Source dataset
uspto-grants-2010_11
Patent number
US07838529B2

Reaction notes

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