Trifluoroacetic acid → HCID 178441324, compound

HRID 82775Notes

Reaction equation

HRID 82775 reaction equation
[Si]([O:8][CH2:9][C@H:10]([NH:41]C(=O)OC(C)(C)C)[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=1[C:23](/[N:25]=[C:26]1\[S:27][C:28]([C:37]([CH3:40])([CH3:39])[CH3:38])=[CH:29][N:30]\1[CH2:31][C@H:32]1[CH2:36][CH2:35][CH2:34][O:33]1)=[O:24])(C(C)(C)C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:41][C@H:10]([CH2:9][OH:8])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:22])[F:21])=[CH:15][C:14]=1[C:23](/[N:25]=[C:26]1\[S:27][C:28]([C:37]([CH3:40])([CH3:39])[CH3:38])=[CH:29][N:30]\1[CH2:31][C@H:32]1[CH2:36][CH2:35][CH2:34][O:33]1)=[O:24]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178454222HCID 178454222, compound

Product 1

HCID 178441324HCID 178441324, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 69A (500 mg, 0.7 mmol) in CH2Cl2 (10 mL) at 0° C. was treated with trifluoroacetic acid (0.27 mL, 3.5 mmol). The mixture was allowed to warm to room temperature and stirred for 3 hours. The mixture was concentrated under reduced pressure, diluted with saturated NaHCO3 and extracted with EtOAc. The organic layer was washed with brine, dried with MgSO4, filtered, and concentrated under reduced pressure. Purification by chromatography (SiO2, eluted with CH2Cl2-MeOH: 6:1) afforded 260 mg of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.33 (s, 9 H), 1.58-1.73 (m, 1H), 1.75-2.04 (m, 3 H), 2.25-2.43 (m, 1 H), 3.08 (q, J=5.6 Hz, 1 H), 3.36-3.53 (m, 3 H), 3.59-3.69 (m, 1 H), 3.74-3.86 (m, 1 H), 3.94-4.01 (m, 1 H), 4.05-4.12 (m, 1 H), 4.19-4.36 (m, 3 H), 4.68 (t, J=5.2 Hz, 1 H), 7.24-7.34 (m, 2 H), 7.76 (dd, J=8.9, 2.2 Hz, 1 H), 8.07 (d, J=2.4 Hz, 1 H); MS (DCI/NH3) m/z 502 (M+H)+. Anal calculated for C23H30F3N3O4S.0.75H2O: C, 53.63; H, 6.16; N, 8.16. Found: C, 53.40; H, 6.06; N, 8.16.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additiondiluted with saturated NaHCO3
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification
  9. washby chromatography (SiO2, eluted with CH2Cl2-MeOH: 6:1)

Sources & evidence

ORD record
ord-26fbb97f149c43b685eeba98a076c15e
Source dataset
uspto-grants-2014_09
Patent number
US08846730B2

Reaction notes

Loading…