Trifluoroacetic acid → HCID 44231735, compound

HRID 2059750Notes

Reaction equation

HRID 2059750 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][CH2:6][C:5]3([CH2:29][CH2:28][CH2:27][CH2:26]3)[C:4]=2[N:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:18][NH:17][C@@H:14]1[CH2:15][CH2:16][N:12]([C:10]2[C:9]3[CH2:8][CH2:7][CH2:6][C:5]4([CH2:29][CH2:28][CH2:27][CH2:26]4)[C:4]=3[N:3]=[C:2]([NH2:1])[N:11]=2)[CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68800064HCID 68800064, compound

Product 1

HCID 44231735HCID 44231735, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of Example 1G (38 mg, 0.09 mmol) in CH2Cl2 (2 mL) was treated with trifluoroacetic acid (0.1 mL) at ambient temperature, and the reaction was stirred for 16 hours. The mixture was diluted with CH2Cl2 (20 mL) and washed with 1N NaOH and water. The organic layer was dried (MgSO4) and concentrated under reduced pressure, and the resulting residue was chromatographed on silica gel (0.8:7.2:92 NH4OH/MeOH/CH2Cl2, eluant) to provide the title product. 1H NMR (300 MHz, CD3OD) δ 3.55-3.78 (m, 3 H), 3.37-3.44 (m, 1 H), 3.22 (t, 1 H), 2.57-2.65 (m, 2 H), 2.38-2.41 (m, 3 H), 2.02-2.17 (m, 3 H), 1.51-1.91 (m, 11 H). MS (DCI+) m/z 302 (M+H).

Workup

  1. washwashed with 1N NaOH and water
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customthe resulting residue was chromatographed on silica gel (0.8:7.2:92 NH4OH/MeOH/CH2Cl2, eluant)

Sources & evidence

ORD record
ord-ee5cb3297666451da197b08bc6509bda
Source dataset
uspto-grants-2012_10
Patent number
US08278313B2

Reaction notes

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