Trifluoroacetic acid → HCID 44538420, compound

HRID 2059720Notes

Reaction equation

HRID 2059720 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([N:12]2[CH2:16][CH2:15][C@@H:14]([NH:17]C(=O)OC(C)(C)C)[CH2:13]2)[C:9]2[CH2:8][CH2:7][C:6]3[O:25][CH:26]4[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]4[C:5]=3[C:4]=2[N:3]=1.FC(F)(F)C(O)=O.[OH-].[Na+]>ClCCl>[NH2:17][C@@H:14]1[CH2:15][CH2:16][N:12]([C:10]2[C:9]3[C:4](=[C:5]4[CH:27]5[CH2:28][CH2:29][CH2:30][CH2:31][CH:26]5[O:25][C:6]4=[CH:7][CH:8]=3)[N:3]=[C:2]([NH2:1])[N:11]=2)[CH2:13]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 86635262HCID 86635262, compound

Product 1

HCID 44538420HCID 44538420, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the product from Example 7A (28 mg, 0.065 mmol) in dichloromethane (2 mL) was treated with trifluoroacetic acid (0.2 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 dehydrogenated material as the major product and title compound: 1H NMR (CD3OD) δ 1.00-1.18 (m, 1H), 1.27-1.41 (m, 1H), 1.45-1.58 (m, 1H), 1.62-1.75 (m, 2H), 1.92-2.07 (m, 3H), 2.11-2.24 (m, 1H), 2.24-2.39 (m, 2H), 3.38-3.52 (m, 1H), 3.74-3.92 (m, 2H), 3.98-4.12 (m, 1H), 4.10-4.24 (m, 2H), 6.87 (d, 1H), 8.08 (d, 1H); MS (DCl/NH3) m/z 326 (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-f93ed6591b19456693c12cddfaecf403
Source dataset
uspto-grants-2012_10
Patent number
US08278311B2

Reaction notes

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