Acetic Acid → HCID 135890157, compound

HRID 539879Notes

Reaction equation

HRID 539879 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH2:20][CH2:21][CH3:22])=[C:6]([C:8]2[NH:13][C:12](=[O:14])[C:11]([CH2:15][CH3:16])=[C:10]([CH2:17][CH3:18])[N:9]=2)[CH:7]=1.[CH3:23][C:24](=O)[CH2:25][CH2:26][C:27](=O)[CH3:28].C(O)(=O)C>C(O)C>[CH3:28][C:27]1[N:1]([C:2]2[CH:3]=[CH:4][C:5]([O:19][CH2:20][CH2:21][CH3:22])=[C:6]([C:8]3[NH:13][C:12](=[O:14])[C:11]([CH2:15][CH3:16])=[C:10]([CH2:17][CH3:18])[N:9]=3)[CH:7]=2)[C:24]([CH3:23])=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 80352,5-HexanedioneHCID 136197415HCID 136197415, compound

Product 1

HCID 135890157HCID 135890157, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The compound (200 mg, 0.66 mmol) of example 42 and 2,5-hexanedione (76 mg, 0.66 mmol) were dissolved in ethanol (10 ml) and added with glacial acetic acid (0.1 ml), followed by refluxing for 12 h. The reaction mixture was concentrated to dryness, dissolved in CH2Cl2 (10 ml), and washed with saturated NaHCO3 (10 ml) and saturated saline (10 ml), dried and concentrated. The residue was passed through a silica gel column to give the title compound (110 mg, yield: 44%). 1H NMR (CDCl3) δ: 11.20 (1H, br), 8.42 (1H, d), 7.30 (1H, dd), 7.10 (1H, d), 5.93 (2H, s), 4.23 (2H, t), 2.63 (2H, q), 2.59 (2H, q), 2.06 (6H, s), 2.04 (2H, m), 1.24 (3H, t), 1.18 (3H, t), 1.15 (3H, t).

Workup

  1. temperatureby refluxing for 12 h
  2. concentrationThe reaction mixture was concentrated to dryness
  3. dissolutiondissolved in CH2Cl2 (10 ml)
  4. washwashed with saturated NaHCO3 (10 ml) and saturated saline (10 ml)
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f4864c18f916415bab595628d0c51150
Source dataset
uspto-grants-2014_10
Patent number
US08871777B2

Reaction notes

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