Trifluoroacetic acid → HCID 87555139, compound

HRID 2111426Notes

Reaction equation

HRID 2111426 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]2[C:17]([N+:18]([O-])=O)=[CH:16][N:15]=[C:14]([Cl:21])[N:13]=2)[CH2:7]1)=[O:5])[CH3:2].FC(F)(F)C(O)=O.[OH-].[Na+]>C(OCC)(=O)C>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]2[C:17]([NH2:18])=[CH:16][N:15]=[C:14]([Cl:21])[N:13]=2)[CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 87618670HCID 87618670, compound

Product 1

HCID 87555139HCID 87555139, compoundYield 9.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To an ice cooled mixture of 1 g (0.0032 mole) of (rac)-1-(2-chloro-5-nitro-pyrimidin-4-yl)-piperidine-3-carboxylic acid ethyl ester (IV-67), 1.96 mL of trifluoracetic acid and 15 mL of ethyl acetate, was added 2.76 g (0.02 mole) of stannous chloride dihydrate. The mixture was stirred overnight at ambient temperature. The mixture was made basic (pH 14) by the addition of 15% sodium hydroxide solution. The mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 0.086 g of (rac)-1-(5-amino-2-chloro-pyrimidin-4-yl)-piperidine-3-carboxylic acid ethyl ester (V-67).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fef91dd2ed0649c9b64b1fad2fa58152
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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