Trifluoroacetic acid → HCID 22500564, compound

HRID 1815449Notes

Reaction equation

HRID 1815449 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][NH:16][S:17]([C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1)(=[O:19])=[O:18])=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[NH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][NH:16][S:17]([C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1)(=[O:19])=[O:18]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22500637HCID 22500637, compound

Product 1

HCID 22500564HCID 22500564, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of the product of step c (3.29 g, 7.89 mmol) in CHCl3 (8 ml) was added trifluoroacetic acid (16 ml) and the reaction mixture was stirred at ambient temperature for 20 h. The excess trifluoroacetic acid was removed at reduced pressure and the residue partitioned between aqueous 10% potassium carbonate (50 ml) and CHCl3 (50 ml). The CHCl3 layer was removed and the aqueous phase was extracted with further CHCl3 (50 ml). The combined organic phases were washed with brine and dried over anhydrous sodium sulfate. The filtrate was evaporated at reduced pressure to afford the title compound (2.42 g, 97%). 1H NMR (CHCl3) 8.43 (1H, d, 1.5), 7.98-7.86 (4H, m), 7.76-7.60 (2H, m), 3.20-3.01 (5H, m), 2.60-2.55 (2H, m), 1.60-1.19 (8H, m).

Workup

  1. customThe excess trifluoroacetic acid was removed at reduced pressure
  2. customthe residue partitioned between aqueous 10% potassium carbonate (50 ml) and CHCl3 (50 ml)
  3. customThe CHCl3 layer was removed
  4. extractionthe aqueous phase was extracted with further CHCl3 (50 ml)
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe filtrate was evaporated at reduced pressure

Sources & evidence

ORD record
ord-b9d361dd7cd14265a2639d803de7e842
Source dataset
uspto-grants-2005_04
Patent number
US06878736B1

Reaction notes

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