Trifluoroacetic acid → HCID 178490674, compound

HRID 556687Notes

Reaction equation

HRID 556687 reaction equation
[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:11](=[O:21])[C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2[O:19][CH3:20])/[N:7]([CH2:22][C@@H:23]2[CH2:26][CH2:25][N:24]2C(OC(C)(C)C)=O)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O>C(Cl)Cl>[NH:24]1[CH2:25][CH2:26][C@@H:23]1[CH2:22][N:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[S:9]/[C:8]/1=[N:10]\[C:11](=[O:21])[C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[O:19][CH3:20]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178490675HCID 178490675, compound

Product 1

HCID 178490674HCID 178490674, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 15B (295 mg, 0.6 mmol) in CH2Cl2 (5 mL) was treated with trifluoroacetic acid (1 mL) and the reaction mixture was stirred at room temperature for 48 hrs, concentrated on the rotovap and the residue was partitioned between ethyl acetate and saturated NaHCO3. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography using an Analogix® Intelliflash280™ (SiO2, 0-15% methanol in CH2Cl2) to afford the title compound (160 mg, 68% yield). MS (DCI) m/z 394 (M+H)+. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.17-1.27 (m, 2H), 1.28-1.35 (s, 9H), 2.05-2.19 (m, 1H), 2.19-2.34 (m, 1H), 3.45-3.61 (m, 1H), 3.72-3.82 (m, 3H), 4.20-4.35 (m, 3H), 7.11 (d, J=8.7 Hz, 1H), 7.30 (s, 1H), 7.45 (dd, J=8.7, 2.8 Hz, 1H), 7.61 (d, J=2.8 Hz, 1H). MS (DCI) m/z 394 (M+H)+.

Workup

  1. concentrationconcentrated on the rotovap
  2. customthe residue was partitioned between ethyl acetate and saturated NaHCO3
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-c4086bb97dcd4fc2aeb0b74b30430cd9
Source dataset
uspto-grants-2011_11
Patent number
US08058293B2

Reaction notes

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