Trifluoroacetic acid → HCID 60146159, compound

HRID 2063242Notes

Reaction equation

HRID 2063242 reaction equation
C([O:5][C:6](=[O:34])[CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][C:27]([O:29]C(C)(C)C)=[O:28])(C)(C)C.FC(F)(F)C(O)=O>C1(OC)C=CC=CC=1>[C:6]([CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])([OH:34])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18374585HCID 18374585, compound

Product 1

HCID 60146159HCID 60146159, compound

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

A solution of 3-{2-[2-(2-{2-[2-(2-tert-Butoxycarbonyl-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-propionic acid tert-butyl ester (6 g, 18.6 mmol) in anisole (20 ml) was cooled in an ice bath and trifluoroacetic acid (65 g) was added. After 3 hrs at RT volatiles were removed under reduced pressure and the residue was partitioned between ethyl acetate (50 ml) and 5% sodium bicarbonate solution. The aqueous layer was acidified with 1 N HCl, saturated with NaCl and then extracted with ethyl acetate (3×50 ml). Combined organic layers were washed with brine and dried over sodium sulfate. Removal of volatiles under the reduced pressure provided the product as colorless liquid which solidified upon refrigeration (3.8 g, 82%).

Workup

  1. customAfter 3 hrs at RT volatiles were removed under reduced pressure
  2. customthe residue was partitioned between ethyl acetate (50 ml) and 5% sodium bicarbonate solution
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. washCombined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. customRemoval of volatiles under the reduced pressure

Sources & evidence

ORD record
ord-c5fd728adeaf417da7eabd629d230f1d
Source dataset
uspto-grants-2012_10
Patent number
US08288349B2

Reaction notes

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