Trifluoroacetic acid → HCID 69412355, compound

HRID 916551Notes

Reaction equation

HRID 916551 reaction equation
C([O:5][C:6](=[O:26])[CH2:7][CH2:8][N:9]([CH2:11][CH2:12][CH:13]1[C:25]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:19]2[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH3:10])(C)(C)C.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>ClCCl>[CH:15]1[C:14]2[CH:13]([CH2:12][CH2:11][N:9]([CH3:10])[CH2:8][CH2:7][C:6]([OH:26])=[O:5])[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]=2[CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 69411015HCID 69411015, compound

Product 1

HCID 69412355HCID 69412355, compoundYield 119%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-{[2-(9H-fluoren-9-yl)-ethyl]-methyl-amino}-propionic acid tert-butyl ester (11.4 g) in 20 ml dichloromethane is cooled to 0°. Trifluoroacetic acid (20 ml) is added and the solution stirred at room temperature over night. To this mixture a 1 M aq. NaHCO3 solution (262 ml) is added dropwise under vigorous stirring. The phases are separated, the water phase acidified with 14 ml 2N HCl and extracted several times with dichloromethane. The combined extracts are dried over sodium sulfate, filtered and evaporated to afford 11.4 g (100%) of a light brown foam which is used without purification. TLC (silicagel, dichloromethane/methanol 85:15): rf 0.3.

Workup

  1. customThe phases are separated
  2. extractionextracted several times with dichloromethane
  3. dry with materialThe combined extracts are dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-bbadbfe060af42c5871fc266f6eeeb2b
Source dataset
uspto-grants-2007_09
Patent number
US07271168B2

Reaction notes

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