Trifluoroacetic acid → HCID 82345154, compound

HRID 2239555Notes

Reaction equation

HRID 2239555 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][NH:14]C(OC(C)(C)C)=O)=[CH:8][CH:7]=1)(=[O:4])=[O:3].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][NH2:14])=[CH:8][CH:7]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86625869HCID 86625869, compound

Product 1

HCID 82345154HCID 82345154, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-{2-[(tert-Butoxycarbonyl)amino]ethyl}phenyl methanesulfonate (3.98 g, 12.62 mmol) was dissolved in DCM (12 mL) and TFA (10 mL) and stirred at rt for 4 h. The reaction mixture was concentrated and redissolved in EtOAc, washed with saturated aqueous K2CO3, and the organic phase was dried with Na2SO4, filtered and evaporated affording the title compound (2.71 g, 99.8%). 1H NMR (500 MHz, CD3OD): δ 2.79 (t, 2H), 2.89 (t, 2H), 3.21 (s, 3H), 7.26 (d, 2H), 7.32 (d, 2H); 13C NMR (125 MHz, CD3OD): δ 36.24, 38.34, 42.95, 122.11, 130.19, 139.44, 148.28; Mass Spectrum: M+H+ 216.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionredissolved in EtOAc
  3. washwashed with saturated aqueous K2CO3
  4. dry with materialthe organic phase was dried with Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-c0d83fc13f3d4897883dc18c6caa5d8d
Source dataset
uspto-grants-2010_05
Patent number
US07723333B2

Reaction notes

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