Trifluoroacetic acid → HCID 59128834, compound

HRID 2390501Notes

Reaction equation

HRID 2390501 reaction equation
[C:1]([C:5]1[CH:20]=[CH:19][CH:18]=[CH:17][C:6]=1[O:7][C:8]1[C:13]([N:14]=[C:15]=[S:16])=[CH:12][CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].C(OC(=O)[NH:27][NH2:28])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[C:1]([C:5]1[CH:20]=[CH:19][CH:18]=[CH:17][C:6]=1[O:7][C:8]1[C:13]([NH:14][C:15](=[S:16])[NH:27][NH2:28])=[CH:12][CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 70091tert-Butyl carbazateHCID 59857388HCID 59857388, compound

Product 1

HCID 59128834HCID 59128834, compoundYield 118.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of Example 1a (1 g, 3.51 mmol) and tert-butylcarbazate (465 mg, 3.51 mmol) in DCM (10 mL) was stirred at rt for 2 h. Trifluoroacetic acid (2 mL) was added and mixture was stirred for 2 h. The solvent was removed and the residue was dissolved in EtOAc (15 mL), washed with saturated sodium bicarbonate solution, dried (anh. MgSO4), filtered and evaporated to give the title compound (1.32 g) as a brown solid. (M+H)+=317.

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in EtOAc (15 mL)
  3. washwashed with saturated sodium bicarbonate solution
  4. dry with materialdried (anh. MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-2c63d5e691384ece9b89af9d9d4323ac
Source dataset
uspto-grants-2012_09
Patent number
US08273772B2

Reaction notes

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