Acetic Acid → HCID 131728435, compound

HRID 1172467Notes

Reaction equation

HRID 1172467 reaction equation
[CH2:1]([CH2:5][C:6](=O)[CH3:7])[C:2]([CH3:4])=O.C(O)(=O)C.[NH2:13][C:14]1[CH:34]=[C:33]([CH3:35])[C:17]2[O:18][C:19]3[C:28]([CH3:29])=[CH:27][C:26]([C:30]([OH:32])=[O:31])=[CH:25][C:20]=3[S:21](=[O:24])(=[O:23])[CH2:22][C:16]=2[CH:15]=1>C1(C)C=CC=CC=1>[CH3:7][C:6]1[N:13]([C:14]2[CH:34]=[C:33]([CH3:35])[C:17]3[O:18][C:19]4[C:28]([CH3:29])=[CH:27][C:26]([C:30]([OH:32])=[O:31])=[CH:25][C:20]=4[S:21](=[O:24])(=[O:23])[CH2:22][C:16]=3[CH:15]=2)[C:2]([CH3:4])=[CH:1][CH:5]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 80352,5-HexanedioneHCID 131728436HCID 131728436, compound

Product 1

HCID 131728435HCID 131728435, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Acetonylacetone (0.040 g, 0.35 mmol)) and acetic acid (0.1 mL, 1.7 mmol) were added to a solution of the methylester of Example 36j in toluene (10 mL). The reaction mixture was refluxed for 6 h, concentrated and triturated with PE60-80° C. The organic extract was concentrated and the crude obtained was purified using flash chromatography (silica gel, EtOAc/PE60-80° C.). It was then subjected to hydrolysis as described in Example 1i to obtain the title compound (J. Chem. Soc., Chem. commun., 800-801, (1982)). Yield: 51%; 1H NMR (DMSO-d6): δ 2.0 (s, 6H, 2CH3), 2.40 (s, 3H, CH3), 2.65 (s, 3H, CH3), 5.20 (s, 2H, CH2), 5.70 (s, 2H, pyrrolyl), 7.30 (s, 1H, Ar), 7.35 (s, 1H, Ar), 8.20 (s, 1H, Ar), 8.35 (s, 1H, Ar); MS: m/e (ES+) 411 (M+).

Workup

  1. temperatureThe reaction mixture was refluxed for 6 h
  2. concentrationconcentrated
  3. customtriturated with PE60-80° C
  4. extractionThe organic extract
  5. concentrationwas concentrated
  6. customthe crude obtained
  7. customwas purified
  8. customflash chromatography (silica gel, EtOAc/PE60-80° C.)
  9. customIt was then subjected to hydrolysis

Sources & evidence

ORD record
ord-22ecf985323b41dbbb6ecf33fca5b5dc
Source dataset
uspto-grants-2010_11
Patent number
US07834001B2

Reaction notes

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