Trifluoroacetic acid → HCID 59737430, compound

HRID 1907699Notes

Reaction equation

HRID 1907699 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[C:19]([NH:21][C:22]3[CH:27]=[C:26]([C:28]4[S:29][CH:30]=[CH:31][CH:32]=4)[CH:25]=[CH:24][C:23]=3[NH:33]C(=O)OC(C)(C)C)=[O:20])=[CH:13][CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:33][C:23]1[CH:24]=[CH:25][C:26]([C:28]2[S:29][CH:30]=[CH:31][CH:32]=2)=[CH:27][C:22]=1[NH:21][C:19](=[O:20])/[CH:18]=[CH:17]/[C:14]1[CH:15]=[N:16][C:11]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59737232HCID 59737232, compound

Product 1

HCID 59737430HCID 59737430, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 41 (85.2 mg, 0.15 mmol) in DCM (2 mL) was added neat trifluoroacetic acid (0.7 mL). The reaction was allowed to stir at room temperature for 2 h then concentrated, diluted with AcOEt, washed with saturated aqueous NaHCO3, brine, dried over MgSO4, filtered and concentrated to give title compound 42 (38 mg, 54% yield).

Workup

  1. concentrationthen concentrated
  2. additiondiluted with AcOEt
  3. washwashed with saturated aqueous NaHCO3, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c13bf4df97374e1cb08e905831d11299
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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