Trifluoroacetic acid → HCID 11620509, compound

HRID 1726959Notes

Reaction equation

HRID 1726959 reaction equation
FC(F)(F)C(O)=O.[C:8]1([CH2:18][N:19]2[C:28](=[O:29])[C:27]3[N:26]([CH2:30][C:31]#[C:32][CH3:33])[C:25]([N:34]4[CH2:39][CH2:38][CH2:37][CH:36]([NH:40]C(OC(C)(C)C)=O)[CH2:35]4)=[N:24][C:23]=3[N:22]([CH2:48][C:49]([O:51][CH3:52])=[O:50])[C:20]2=[O:21])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[C:8]1([CH2:18][N:19]2[C:28](=[O:29])[C:27]3[N:26]([CH2:30][C:31]#[C:32][CH3:33])[C:25]([N:34]4[CH2:39][CH2:38][CH2:37][CH:36]([NH2:40])[CH2:35]4)=[N:24][C:23]=3[N:22]([CH2:48][C:49]([O:51][CH3:52])=[O:50])[C:20]2=[O:21])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 68849072HCID 68849072, compound

Product 1

HCID 11620509HCID 11620509, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.7 ml of trifluoroacetic acid are added to a solution of 200 mg 1-(naphth-1-ylmethyl)-3-(methoxycarbonylmethyl)-7-(but-2-ynyl)-8-(3-tert-butoxycarbonylamino-piperidin-1-yl)-xanthine in 3 ml dichloromethane. The solution is stirred for 3 h at ambient temperature and then added to ice-cooled aqueous potassium carbonate solution. The aqueous phase is extracted with dichloromethane, the combined organic extracts are dried over sodium sulphate, and the solvent is removed. The residue is purified by chromatography on a silica gel column with methylene chloride/methanol (7:3) as eluant.

Workup

  1. additionadded to ice-
  2. extractionThe aqueous phase is extracted with dichloromethane
  3. dry with materialthe combined organic extracts are dried over sodium sulphate
  4. customthe solvent is removed
  5. customThe residue is purified by chromatography on a silica gel column with methylene chloride/methanol (7:3) as eluant

Sources & evidence

ORD record
ord-1b7d292cf0e74357af44d767a5bd7ef0
Source dataset
uspto-grants-2009_02
Patent number
US07495003B2

Reaction notes

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