Trifluoroacetic acid → HCID 60146159, compound

HRID 1402657Notes

Reaction equation

HRID 1402657 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.

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

Sources & evidence

ORD record
ord-e5cf2df626e744c0bdfbb721818cd2e9
Source dataset
uspto-grants-2014_12
Patent number
US08912148B2

Reaction notes

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