Trifluoroacetic acid → HCID 66714093, compound

HRID 2173764Notes

Reaction equation

HRID 2173764 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][C:18]([O:20]C(C)(C)C)=[O:19])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:1]1([CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66716176HCID 66716176, compound

Product 1

HCID 66714093HCID 66714093, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1 g of tert-butyl 3-{2-[2-(2-morpholin-4-yl-ethoxy)-ethoxy]-ethoxy}-propanoate in 50 ml of DCM was added 4 ml of TFA. The mixture was stirred for 10 hours at room temperature and then concentrated under reduced pressure and purified on a Mega BE-SCX, 25GM 150ML cartridge (Varian), using washing with MeOH and detachment of the expected product with a 2N solution of ammonia in MeOH. The fractions containing the desired product were combined and concentrated under reduced pressure. 830 mg of 3-{2-[2-(2-morpholin-4-yl-ethoxy)-ethoxy]-ethoxy}-propanoic acid were obtained. LC/MS (E): tr (ELSD)=0.16 min; [M+H]+: m/z 292

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified on a Mega BE-SCX, 25GM 150ML cartridge (Varian)
  3. washusing washing with MeOH and detachment of the expected product with a 2N solution of ammonia in MeOH
  4. additionThe fractions containing the desired product
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-34f9624ce5e64cbbb4ef9bb13ec151a5
Source dataset
uspto-grants-2015_06
Patent number
US09056914B2

Reaction notes

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