Acetic Acid → HCID 86699871, compound

HRID 1772144Notes

Reaction equation

HRID 1772144 reaction equation
[C:1]([O:4][CH2:5][C:6]1[C:11]([C:12]2[CH:17]=[C:16]([N+:18]([O-])=O)[C:15](=[O:21])[N:14]([CH3:22])[CH:13]=2)=[CH:10][CH:9]=[CH:8][C:7]=1[N:23]1[CH2:31][C:30]2[C:25](=[CH:26][CH:27]=[C:28]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH:29]=2)[C:24]1=[O:36])(=[O:3])[CH3:2].C(O)(=O)C>[Zn].C1COCC1>[C:1]([O:4][CH2:5][C:6]1[C:7]([N:23]2[CH2:31][C:30]3[C:25](=[CH:26][CH:27]=[C:28]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH:29]=3)[C:24]2=[O:36])=[CH:8][CH:9]=[CH:10][C:11]=1[C:12]1[CH:17]=[C:16]([NH2:18])[C:15](=[O:21])[N:14]([CH3:22])[CH:13]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 86699870HCID 86699870, compound

Product 1

HCID 86699871HCID 86699871, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A 50-mL single-neck round-bottomed flask equipped with a magnetic stirrer was purged with nitrogen and charged with 122c (600 mg, 1.23 mmol), acetic acid (10 mL) and THF (5 ml). Zinc dust (1.56 g, 20.5 mmol) was added in portions. The reaction mixture was stirred at room temperature for 1 h. After this time, the reaction mixture was filtered, and the filtrate was evaporated under reduced pressure. The resulting residue was purified by flash chromatography to afford a 81% (460 mg) yield of 122d as a yellow oil: 1H NMR (500 MHz, CDCl3) δ 7.85 (d, 1H, J=8.0 Hz), 7.58 (d, 1H, J=8.0 Hz), 7.52 (s, 1H), 7.45 (t, 1H, J=8.0 Hz), 7.28 (d, 2H, J=8.0 Hz), 6.74 (d, 1H, J=2.0 Hz), 6.57 (d, 1H, J=2.0 Hz), 5.08 (s, 2H), 4.78 (s, 2H), 4.37 (s, 2H), 3.60 (s, 3H), 1.85 (s, 3H), 1.40 (s, 9H); MS (ESI+) m/z 460.3 (M+H).

Workup

  1. customA 50-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. customwas purged with nitrogen
  3. filtrationAfter this time, the reaction mixture was filtered
  4. customthe filtrate was evaporated under reduced pressure
  5. customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-9c5899e1a1a44d9484834e82b5a5c812
Source dataset
uspto-grants-2016_02
Patent number
US09249123B2

Reaction notes

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