Trifluoroacetic acid → HCID 57786843, compound

HRID 424622Notes

Reaction equation

HRID 424622 reaction equation
C([SiH](CC)CC)C.FC(F)(F)C(O)=O.C([O:19][C:20](=[O:41])[CH2:21][O:22][CH2:23][CH2:24][N:25]([S:27]([C:30]1[C:35]([CH3:36])=[CH:34][C:33]([O:37][CH3:38])=[C:32]([CH3:39])[C:31]=1[CH3:40])(=[O:29])=[O:28])[CH3:26])(C)(C)C>>[CH3:38][O:37][C:33]1[CH:34]=[C:35]([CH3:36])[C:30]([S:27]([N:25]([CH3:26])[CH2:24][CH2:23][O:22][CH2:21][C:20]([OH:41])=[O:19])(=[O:28])=[O:29])=[C:31]([CH3:40])[C:32]=1[CH3:39]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 57786870HCID 57786870, compound

Product 1

HCID 57786843HCID 57786843, compound

Procedure

First triethylsilane (1.12 g, 1.54 ml, 9.6 mmol) and then trifluoroacetic acid (5 ml) were added to a solution of {2-[(4-methoxy-2,3,6-trimethylbenzenesulfonyl)-methylamino]-ethoxy}-acetic acid tert-butyl ester (2.48 g, 6.18 mmol) in MC (50 ml) and the mixture was stirred at RT for 5 h. The mixture was then concentrated i. vac., and the residue was taken up repeatedly in toluene and the mixture in each case concentrated again. The crude product was dissolved in EtOAc and the solution was extracted with 5% strength NaHCO3 soln. (3×50 ml). The combined aqueous phases were adjusted to pH 1 with conc. hydrochloric acid and extracted again with EtOAc (3×50 ml). The combined EtOAc phases were dried with Na2SO4 and concentrated i. vac. Yield: 2.41 g (>99%)

Workup

  1. concentrationThe mixture was then concentrated i
  2. concentrationthe mixture in each case concentrated again
  3. dissolutionThe crude product was dissolved in EtOAc
  4. extractionthe solution was extracted with 5% strength NaHCO3 soln
  5. extractionextracted again with EtOAc (3×50 ml)
  6. dry with materialThe combined EtOAc phases were dried with Na2SO4
  7. concentrationconcentrated i

Sources & evidence

ORD record
ord-6f080ac2a11541779e0ac41e7de15838
Source dataset
uspto-grants-2012_01
Patent number
US08106055B2

Reaction notes

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