Trifluoroacetic acid → HCID 178441297, compound

HRID 76263Notes

Reaction equation

HRID 76263 reaction equation
[CH2:1]([C:5]1=[CH:6][N:7]([C:29]([CH3:32])([CH3:31])[CH3:30])[S:8]/[C:9]/1=[N:10]\[C:11]([C:13]1[CH:14]=[C:15]([NH:21]C(=O)OC(C)(C)C)[CH:16]=[CH:17][C:18]=1[O:19][CH3:20])=[O:12])[CH2:2][CH2:3][CH3:4].C(O)(C(F)(F)F)=O>>[NH2:21][C:15]1[CH:16]=[CH:17][C:18]([O:19][CH3:20])=[C:13]([CH:14]=1)[C:11](/[N:10]=[C:9]1/[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[CH:6][N:7]([C:29]([CH3:31])([CH3:32])[CH3:30])[S:8]/1)=[O:12]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178441300HCID 178441300, compound

Product 1

HCID 178441297HCID 178441297, compoundYield 94.1%

Procedure

The product from Example 55A (71 mg, 0.15 mmol) was treated with TFA (1 mL) at rt for 10 min, solvent removed and the mixture treated with saturated aqueous NaHCO3, and extracted with EtOAc (2×). The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-50% Hexane in ethyl acetate) to afford 51 mg (92%) of the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 0.97 (t, J=7.32 Hz, 3 H) 1.36-1.47 (m, 2 H) 1.64 (s, 9 H) 1.67-1.77 (m, 2 H) 2.83 (dd, J=7.93 Hz, 2 H) 3.49 (brs, 2 H) 3.87 (s, 3 H) 6.76 (dd, J=8.54, 3.05 Hz, 1 H) 6.83 (d, J=8.54 Hz, 1 H) 7.54 (d, J=2.75 Hz, 1 H) 7.90 (s, 1 H); MS (DCI/NH4+) m/z 362 (M+H)+.

Workup

  1. customsolvent removed
  2. additionthe mixture treated with saturated aqueous NaHCO3
  3. extractionextracted with EtOAc (2×)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-7a764e8706c5405585c35a156193d333
Source dataset
uspto-grants-2014_09
Patent number
US08835475B2

Reaction notes

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