Trifluoroacetic acid → HCID 66595123, compound

HRID 1092287Notes

Reaction equation

HRID 1092287 reaction equation
FC(F)(F)C(O)=O.C(OC([CH2:15][NH:16][C:17]1[CH:18]=[C:19]([C:23]2[CH:24]=[N:25][C:26]([CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[N:27][CH:28]=2)[CH:20]=[CH:21][CH:22]=1)=O)(C)(C)C.[OH-].[Na+]>ClCCl>[CH3:15][NH:16][C:17]1[CH:18]=[C:19]([C:23]2[CH:28]=[N:27][C:26]([CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[N:25][CH:24]=2)[CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 66590676HCID 66590676, compound

Product 1

HCID 66595123HCID 66595123, compoundYield 187.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.12 ml (1.6 mmol, 5 eq) of trifluoroacetic acid is added to a solution of 118 mg (0.32 mmol, 1 eq) of methyl 3-{5-[3-(tert-butoxycarbonylmethylamino)phenyl]pyrimidin-2-yl}propanoate in 4 ml of dichloromethane. The reaction mixture is stirred for 16 hours at room temperature. The reaction is stopped by adding 20 mL of 1 N sodium hydroxide solution and is then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on silica gel (99/1 dichloromethane/methanol). 163 mg of methyl 3-[5-(3-methylaminophenyl)pyrimidin-2-yl]propanoate are obtained in the form of a colorless oil. Yield=99%.

Workup

  1. extractionis then extracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. customThe solvents are evaporated off
  4. customthe residue is then chromatographed on silica gel (99/1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-5abeedc3af6d4f44bec521f7144f503d
Source dataset
uspto-grants-2012_03
Patent number
US08129416B2

Reaction notes

Loading…