Trifluoroacetic acid → HCID 12147933, compound

HRID 970413Notes

Reaction equation

HRID 970413 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=1)(=[O:16])=[O:15])(C)(C)C.FC(F)(F)C(O)=O>>[NH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=1)(=[O:15])=[O:16]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 12147932[5-(3-Nitro-benzenesulfonylamino)-pentyl]-carbamic acid-tert-butyl ester

Product 1

HCID 12147933HCID 12147933, compound

Procedure

5.00 g (12.9 mmol) of [5-(3-nitro-benzenesulfonylamino)-pentyl]-carbamic acid-tert-butyl ester is mixed with 15 ml of trifluoroacetic acid and stirred for 90 minutes at room temperature. The reaction mixture is concentrated by evaporation, and the residue is made basic with saturated NaHCO3 solution. Then, it is extracted with ethyl acetate (2×). The combined organic phases are washed with saturated NaCl solution, dried (Na2SO4), filtered and concentrated by evaporation. 3.4 g (11.8 mmol, corresponding to 91% of theory) of the product is obtained.

Workup

  1. concentrationThe reaction mixture is concentrated by evaporation
  2. extractionThen, it is extracted with ethyl acetate (2×)
  3. washThe combined organic phases are washed with saturated NaCl solution
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. custom3.4 g (11.8 mmol, corresponding to 91% of theory) of the product is obtained

Sources & evidence

ORD record
ord-83791e28f8c04412bfba48db4739a8d6
Source dataset
uspto-grants-2007_12
Patent number
US07312225B2

Reaction notes

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