Trifluoroacetic acid → HCID 71231117, compound

HRID 2199577Notes

Reaction equation

HRID 2199577 reaction equation
C(OC([N:8](C(OC(C)(C)C)=O)[CH2:9][CH2:10][C:11]1[CH:15]=[CH:14][S:13][C:12]=1[C:16]1[S:20][C:19]([C:21]2[S:22][CH:23]=[CH:24][C:25]=2[CH2:26][CH2:27][N:28](C(OC(C)(C)C)=O)C(=O)OC(C)(C)C)=[CH:18][CH:17]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][CH2:9][CH2:10][C:11]1[CH:15]=[CH:14][S:13][C:12]=1[C:16]1[S:20][C:19]([C:21]2[S:22][CH:23]=[CH:24][C:25]=2[CH2:26][CH2:27][NH2:28])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67991310HCID 67991310, compound

Product 1

HCID 71231117HCID 71231117, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Intermediate L (208 mg, 0.283 mmol) was dissolved DCM (2 ml) and TFA (2 ml) was added. The mixture was stirred at rt for 1 h. Solvents evaporated and residue dissolved in water. The solution was added 1 M NaOH (2 ml) and the aqueous layer extracted with CHCl3. The combined organic layers were dried (MgSO4) and 1.2 M HCl in EtOH (2 ml) was added. Solvents were evaporated to give the HCl-salt of the title compound. Yield: 105 mg (99%); yellow-orange solid. HPLC: RT=2.68 min, 95% (254 nm, 10-40% MeCN in 0.1% TFA, 3 min, ACE) and RT=2.68 min, 94% (350 nm, 10-40% MeCN in 0.1% TFA, 3 min, ACE). 1H NMR (400 MHz, DMSO-d6): δ 3.06 (br s, 12H), 7.14 (d, J 5.2 Hz, 2H), 7.27 (s, 2H), 7.58 (d, J 5.2 Hz, 2H). LC-MS: m/z=335 (M+1).

Workup

  1. additionwas added
  2. customSolvents evaporated
  3. dissolutionresidue dissolved in water
  4. additionThe solution was added 1 M NaOH (2 ml)
  5. extractionthe aqueous layer extracted with CHCl3
  6. dry with materialThe combined organic layers were dried (MgSO4) and 1.2 M HCl in EtOH (2 ml)
  7. additionwas added
  8. customSolvents were evaporated

Sources & evidence

ORD record
ord-0c32ca7ec8f0494988eed887bf42ff6d
Source dataset
uspto-grants-2016_06
Patent number
US09359311B2

Reaction notes

Loading…