Trifluoroacetic acid → HCID 44538323, compound

HRID 2059718Notes

Reaction equation

HRID 2059718 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([N:12]2[CH2:16][CH2:15][C@@H:14]([N:17](C)[C:18](=O)OC(C)(C)C)[CH2:13]2)[C:9]2[CH2:8][CH2:7][C:6]3[O:26][CH:27]4[CH2:32][CH2:31][CH2:30][CH2:29][CH:28]4[C:5]=3[C:4]=2[N:3]=1.FC(F)(F)C(O)=O.[OH-].[Na+]>ClCCl>[CH3:18][NH:17][C@@H:14]1[CH2:15][CH2:16][N:12]([C:10]2[C:9]3[CH2:8][CH2:7][C:6]4[O:26][CH:27]5[CH2:32][CH2:31][CH2:30][CH2:29][CH:28]5[C:5]=4[C:4]=3[N:3]=[C:2]([NH2:1])[N:11]=2)[CH2:13]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 86635261HCID 86635261, compound

Product 1

HCID 44538323HCID 44538323, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the product from Example 2C (51 mg, 0.115 mmol) in dichloromethane (2 mL) was treated with trifluoroacetic acid (0.18 mL) at ambient temperature and stirred for 16 hours. The mixture was diluted with dichloromethane (20 mL) and basified with sodium hydroxide (1 N). The organic layer was separated, dried with magnesium sulfate, and concentrated under reduced pressure. The resulting residue was chromatographed on a silica gel column eluting with ammonium hydroxide/methanol/dichloromethane (0.8/8/92) to provide the title product: 1H NMR (CD3OD) δ 1.10-1.22 (m, 1H), 1.25-1.36 (m, 1H), 1.42-1.55 (m, 1H), 1.56-1.68 (m, 2H), 1.78-1.90 (m, 1H), 1.95-2.07 (m, 2H), 2.11-2.31 (m, 2H), 2.48 (t, 2H), 2.55-2.60 (m, 3H), 2.98-3.09 (m, 3H), 3.49-3.56 (m, 1H), 3.65-3.77 (m, 2H), 3.80-3.91 (m, 2H), 4.68-4.75 (m, 1H); MS (DCl/NH3) m/z 342 (M+H)+.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried with magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was chromatographed on a silica gel column
  5. washeluting with ammonium hydroxide/methanol/dichloromethane (0.8/8/92)

Sources & evidence

ORD record
ord-597dc84fa17d40bab1d257394d4d24c2
Source dataset
uspto-grants-2012_10
Patent number
US08278311B2

Reaction notes

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